Abstract
Lead tetraacetate (LTA), Pb(OAc)4, is one of the most versatile oxidants in organic chemistry. Depending on the reaction conditions and nature of the substrate, it can be used for selective and partial oxidations of various reactive groupings, but also—and this is of primary importance—for the functionalization of nonactivated carbon atoms. The versatility of LTA originates from its properties: it can act as a radical and/or ionic oxidant and participate in processes involving substitution, elimination, addition, or fragmentation reactions, depending on the functionality and experimental conditions.
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References
G. M. Rubottom, in Oxidation in Organic Chemistry, W. S. Trahanovsky, Ed., Part D, pp. 1–145, Academic Press, New York, 1982.
R. N. Butler, in Synthetic Reagents, J. S. Pizey, Ed., Vol.3, pp. 277–419, Ellis Horwood, Chichester, 1977.
G. W. Rotermund, Blei-Verhindungen als OxidationsmitteL in Methoden der Organischen Chemie (Houben-Weyl) Band 4, Teil lb, Oxidation II, E. Muller, Ed., pp. 204–412, Georg Thieme, Stuttgart, 1975.
R. Griegee, in Oxidation in Organic Chemistry, K. Wiberg, Ed., Part A, pp. 277–366, Academic Press, New York, 1965.
L. F. Fieser and M. Fieser, Reagents for Organic Synthesis 1, 536 (1967); 2, 234 (1969); 3, 168 (1972); 4, 278 (1974); 5, 365 (1975); 6, 313 (1977); 7, 185 (1979); 8, 269 (1980); 9, 265 (1981).
M. Lj. Mihailović and Ž. Ceković, Synthesis. 209 (1970).
M. Lj. Mihailović and R. E. Partch, in Selective Organic Transformations, B.S.Thyagarajan, Ed., Vol.2, pp. 97–182, Wiley-Interscience, New York, 1972.
K. Heusler and J. Kalvoda, Angew. Chem. 76, 518 (1964); Angew. Chem. Internal. Ed. 3, 525 (1964).
J. Kalvoda and K. Heusler, Synthesis. 501 (1971).
K. Heusler and J. Kalvoda, in Steroid Synthesis, J. Fried and J. A. Edwards, Eds., Vol. II, pp. 237–287, Reinhold, New York, 1972.
C. A. Bunton, in Oxidation in Organic Chemistry. K. Wiberg, Ed., Part A, pp. 398–405, Academic, New York, 1965.
A. S. Prelin, Adv. Carhohydr. Chem. 14, 9 (1959).
M. Lj. Mihailović and Ž. Čeković, in The Chemistry of the Hydroxy Group, S. Patai, Ed., Part 1, pp. 505–592. Wiley-lnterscience, New York, 1971.
R. M. Moriarty, in Selective Organic Transformations, B. S. Thyagarajan, Ed., Vol.2, pp. 183–237, Wiley, New York, 1972.
R. A. Sheldon and J. K. Kochi, Org. React. 19, 279 (1972).
J. B. Aylward, Quart. Rev. 25, 407 (1971).
R. N. Butler, F. L. Scott, and T. A. F. O’Mahony, Chem. Rev. 73, 93 (1973).
R. N. Butler, Chem. Ind. 1972, 523.
R. N. Butler, Chem. Ind. 1968, 437.
J. Warkentin, Synthesis 1970, 279.
O. Dimroth, O. Friedemann, and H. Kiimmerer, Ber. Dtsch. Chem. Ges. 53, 481 (1920); J. C. Bailar, Jr., Inorg. Syn. 1, 47 (1939).
O. Dimroth and R. Schweizer. Ber. Dtsch. Chem. Ges. 56, 1375 (1923).
R. E. Oesper and C. L. Deasy, J. Am. Chcm. Soc. 61, 972 1939).
A. I. Vogel. Practical Organic Chemistry, pp. 199, Longmans. London, 1974.
C. D. Hurd and P. R. Austin, J. Am. Chem. Soc. 53. 1543 (1931).
E R. Cole, Chem. Ind. 1959, 544.
B. Kamenar, Acta Crystallogr. 16A, 34 (1963).
E. Detilleux and J. Jadot. Bull. Soc. R. Sci. Liege 24. 366 (1955).
J. Ujhazy and R. E. Cole, Nature 209, 395 (1966).
C. Walling and J. Kjellgren, J. Org. Chem. 34, 1488 (1969).
R. E. Partch, J. Am. Chem. Soc. 89, 3662 (1967).
R. J. Ouellette, A. South, Jr., and D. L. Shaw, J. Am. Chem. Soc. 87, 2602 (1965).
S. Moon. J. Org. Chem. 29, 3456 (1964).
R. Griegee and A. Rimmelin, Chem. Ber. 90, 414 (1957).
R. J. Ouellette and D. L. Shaw, J. Am. Chem. Soc. 86, 1651 (1964).
R. J. Ouellette, D. Miller, A. South, Jr., and R. D. Robins, J. Am. Chem. Soc. 91, 971 (1969).
J. Bornstein and L. Skarlos, J. Chem. Soc. Chem. Commun. 1971, 796.
R. Griegee, Ann. Chem. 481, 263 (1930).
K. B. Wiberg and D. Nielsen, J. Org. Chem. 29, 3353 (1964).
E. Hahl, Ph. D. Dissertation, Technical University of Karlsruhe, West Germany, 1958.
A. Lethbridge, R. O. C. Norman, and C. B. Thomas, J. Chem. Soc. Perkin Trans. I 1974, 1929; 1975, 231.
H. Kropf, J. Gelbrich, and M. Ball, Tetrahedron Lett. 1969, 3427.
E. I. Heiba, R. M. Dessau, and W. J. Koehl, Jr., J. Am. Chem. Soc. 90, 2706 (1968).
R. Criegee, P. Dimroth, K. Noll, R. Simon, and C. Weis, Chem. Ber. 90, 1070 (1957).
Y. Yukawa and N. Nagashi, Bull. Chem. Soc. Jpn 39, 2255 (1966).
H. Hock and H. Kropf, Chem. Ber. 91, 1681 (1958).
E. Zbiral, Synthesis, 285 (1972), and references cited therein.
K. Ichikawa and S. Uemura, J. Org. Chem. 32, 493 (1967).
R. Criegee, Angew. Chem. 70, 173 (1958).
C. B. Anderson and S. Winstein, J. Org. Chem. 28, 605 (1963).
R. Criegee, Angew. Chem. 53, 321 (1940).
H. J. Kabbe, Ann. Chem. 656, 204 (1962).
E. Dane and K. Eder, Ann. Chem. 539, 207 (1939).
A. C. Cope, M. Gordon, S. Moon, and C H. Park, J. Am. Chem. Soc. 87, 3119 (1965).
A. Kergomard, Ann. Chim. (Paris) 8, 153 (1953).
T. Sato, Nippon Kagaku Zasshi 85, 889 (1964); Chem. Abstr. 62, 13181 (1965).
I. Alkonyi, Chem. Ber. 96, 1873 (1963).
M. Mousseron and R. Jacquier, Bull. Soc. Chim. France 1952, 467.
B. Cross and G. H. Whitham, J. Chem. Soc. 1960, 3895.
M. Stefanović, A. Jokic, Z. Maksimović, Lj. Lorenc, and M. Lj. Mihailović, Helv. Chim. Acta 53, 1895 (1970).
E. Zbiral, G. Nestler, and K. Kischa, Tetrahedron 26, 1427 (1970).
E. Zbiral and G. Nestler, Tetrahedron 27, 2293 (1971).
M. Ephritikhine and J. Levisalles, J. Chem. Soc. Chem. Commun. 1974, 429.
K. Alder, F. H. Flock, and H. Wirtz, Chem. Ber. 91, 609 (1958).
R. M. Moriarty and H. Walsh, unpublished results, reported in Ref. 13.
J. Kagan, Helv. Chim. Acta 55, 2356 (1972).
W. F. Erman, J. Org. Chem. 32, 765 (1967).
W. Huckel and H. G. Kirschner, Chem. Ber. 80, 41 (1947).
S. Wakabayashi, Kogyo Kagaku Zasshi 63, 627 (1960); Chem. Abstr. 56, 7165 (1962).
P. Nafla and G. Ourisson, Bull. Soc. Chim. France 1954, 1115.
G. H. Whitham, J. Chem. Soc. 1961, 2232.
Y. Matsubara, Nippon Kagaku Zasshi 78, 907 (1957); Chem. Abstr. 53. 22056 (1959).
L. E. Gruenewald and D. C. Johnson, J. Org. Chem. 30, 1673 (1965).
M. P. Hartshorn and A. F. A. Wallis, J. Chem. Soc. 1964, 5254.
T. Sato, Nippon Kagaku Zasshi 86, 252 (1965); Chem. Abstr. 63, 4335 (1965).
B. A. Arbuzov, V. V. Ratner, and Z. G. Isaeva, Izvest. Akad. Nauk SSSR Ser. Khim 1973, 45; Chem. Abstr. 78, 136413 (1973).
B. A. Arbuzov, V. V. Ratner, Z. G. Isaeva, and M. G. Belyaeva, Dokl. Akad. Nauk SSSR 204, 1115 (1972); Chem. Abstr. 77. 88674 (1972).
R. Criegee and H. Beucker. Ann. Chem. 541. 218 (1939).
S. Uemura, A. Tabeta, M. Okano, and K. Ichikawa. Chem. Commun. 1970, 1630.
T. Posternak and H. Friedli, Hetv. Chim. Acta 36. 251 (1953).
F. V. Brutcher, Jr., and F. J. Vara, J. Am. Chem. Soc. 78. 5695 (1956).
M. Frinkelstein, Chem. Ber. 90, 2097 (1957).
A. Windaus and U. Riemann, Hoppe-Seylers Z. Physiol. Chem. 274, 206 (1942).
A. Windaus, U. Riemann, and G. Zuhlsdorff, Ann. Chem. 552, 135, 142 (1942).
H. Meerwein. Ber. Dtsch. Chem. Ges. 77, 227 (1944).
A. J. Birch, A. R. Murray, and H. Smith, J. Chem. Soc. 1951, 1945.
P. D. Gardner and R. J. Thompson, J. Org. Chem. 22, 36 (1957)
M. S. Newman. J. Am. Chem. Soc. 62, 1683 (1940)
E. Bergmann and F. Bergmann, J. Am. Chem. Soc. 60, 1805 (1938)
C. Weiz-mann, E. Bergmann, and T. Berlin, J. Am. Chem. Soc. 60, 1331 (1938).
I. Tabushi and R. Oda, Tetrahedron Lett. 1966, 2487.
R. D. Bach, R. N. Brummel, and J. W. Holubka, J. Org. Chem. 40, 2559 (1975).
R. D. Bach, U. Mazur, R. N. Brummel, and L. H. Lin. J. Am. Chem. Soc. 93. 7120 (1971).
F. B. La Forge and F. Acree, J. Org. Chem. 6, 208 (1941).
V. Franzen, Chem. Ber. 87, 1478 (1954).
J. Jadot and M. Neuray, Bull. Soc. Roy. Sci. Liege 30, 34. 52, 431 (1961); 31, 247 (1962).
S. Moon and W. Campbell, Chem. Commun. 1966, 470.
R. O. C Norman, C. B. Thomas, and J. S. Willson, J. Chem. Soc. (B) 1971, 518.
J. R. Campbell, J. R. Kalman, J. T. Pinhey, and S. Sternhell, Tetrahedron Lett. 1972, 1763.
H. C. Bell, J. R. Kalman, J. T. Pinhey, and S. Sternhell, Tetrahedron Lett. 1974, 853.
E. I. Heiba, R. M. Dessau, and W. J. Koehl, Jr., J. Am. Chem. Soc. 90, 1082 (1968).
G. W. K. Cavill and D. H. Solomon, J. Chem. Soc. 1954. 3943.
L. F. Fieser, R. C. Clapp, and W. H. Daudt, J. Am. Chem. Soc. 64, 2052 (1942).
R. O. C. Norman and C. B. Thomas, J. Chem. Soc. (B) 1970. 421.
R. O. C. Norman, C. B. Thomas, and J. S. Willson, J. Chem. Soc. Perkin Trans. I 1973. 325.
F. R. Preuss and R. Menzei, Arch. Pharm. 291, 350, 377 (1958).
F. R. Preuss and J. Janshen, Arch. Pharm. 293, 933 (1960).
G. W. K. Cavill and D. H. Solomon, J. Chem. Soc. 1955, 1404.
J. B. Atlward, J. Chem. Soc. (B) 1967, 1268.
B. Rindone and C. Scolastico, J. Chem. Soc. (C) 1971. 3983.
L. F. Fieser and S. T. Putnam, J. Am. Chem. Soc. 69, 1038. 1041 (1947).
L. F. Fieser and E. B. Hershberg, J. Am. Chem. Soc. 60, 1893 (1938).
L. F. Fieser and E. B. Hershberg, J. Am. Chem. Soc. 60, 2542 (1938).
N. Elming and N. Clausson-Kaas, Acta Chem. Scand. 6, 535 (1952).
N. Elming, Acta Chem. Scand. 6, 578 (1952).
N. Elming and N. Clausson-Kaas, Acta Chem. Scand. 6, 565 (1952).
C. K. Dien and R. E. Lutz, J. Org. Chem. 22, 1355 (1957).
P. J. Andrulis, M. J. S. Dewar, R. Dietz, and R. L. Hunt, J. Am. Chem. Soc. 88, 5473 (1966).
M. M. Bokadia, B. R. Brown and W. Cummings, J. Chem. Soc. 1960, 3308.
W. S. Johnson, J. M. Anderson and W. E. Shelberg, J. Am. Chem. Soc. 66, 218 (1944).
G. M. Badger and J. W. Cook, J. Chem. Soc. 1939, 802.
L. F. Fieser and J. Cason, J. Am. Chem. Soc. 62, 432 (1940); J. Cason, Org. Syn. 21, 1 (1941).
D. D. Berge and M. M. Bokadia, J. Indian Chem. Soc. 43, 125 (1966).
B. L. Verma and M. M. Bokadia, J. Indian Chem. Soc. 43, 91 (1966).
G. Dupont, R. Dulon, G. Ourisson, and G. Thibault, Bull. Soc. Chim. France 1955, 708.
K. Mori and M. Matsui, Tetrahedron 26. 3467 (1970).
G. M. Badger, W. Carruthers and J. W. Cook, J. Chem. Soc. 1952, 4996.
W. S. Johnson, A. D. Kemp, R. Pappo, J. Ackerman, and W. F. Johns, J. Am. Chem. Soc. 78, 6312 (1956).
G. W. K. Cavill, A. Robertson, and W. B. Whalley, J. Chem. Soc. 1949, 1567.
W. Siedel and F. Winkler, Ann. Chem. 554, 162 (1943).
R. Criegee, P. Dimroth, K. Noll, R. Simon, and G Weis, Chem. Ber. 90, 1070 (1957).
R. Müller and H. Plieninger, Chem. Ber. 92, 3009 (1959).
C. D. Hurd and O. E. Edwards, J. Org. Chem. 19, 1319 (1954).
H. O. L. Fischer, E. Bear and L. Feldmann, Ber. Dtsch. Chem. Ges. 63, 1732 (1937).
H. Normant C. R. Acad. Sci. Paris 228, 102 (1949).
F. Corbani, B. Rindone, and C. Scolastico, Tetrahedron 29, 3253 (1973).
Ž. Čeković, J. Bosnjak, and M. Cvetković, Tetrahedron Lett. 1980. 2675.
RB Board, J. F. McGhie, M. Robinson, D. H. R. Barton, D. C. Horweil, and R. V. Stick. J. Chem. Soc. Perkin Trans. I 1975, 1237.
R. B. Board, J. F. McGhie, M. Robinson, and D. H. R. Barton, J. Chem. Soc. Perkin Trans. 1975, 1242.
N. Finch, C. W. Gemenden, I. H.-C. Hsu, and W. I. Taylor, J. Am. Chem. Soc. 85, 1520 (1963).
V. M. Mićović, R. I. Mamuzić, D. Jeremić, and M. Lj. Mihailović, Bull. Acad. Serbe Sci. Classe Sci. Math. Natur. Namr. Sci. 11. 161 (1961); Tetrahedron Lett. 1963, 2091: Tetrahedron 20, 2279 (1964).
G. Cainelli, M. Lj. Mihailović, D. Arigoni, and O. Jeger, Helv. Chim. Acta 42, 1124 (1959).
M. Lj. Mihailović, Ž. Čeković, Z. Maksimović, D. Jeremić, Lj. Lorenć, and R. I. Mamuzić, Tetrahedron 21, 2799 (1965).
K. Heusler, J. Kalvoda, Ch. Meystre, P. Wieland, G. Anner, A. Wettstein, G. Cainelli, D. Arigoni, and O. Jeger, Helv. Chim. Acta 44, 502 (1961).
M. Lj. Mihailović, J. Bosnjak, Z. Maksimović, Ž. Čeković, and LJ. Lorenc, Tetrahedron 11955 (1966).
R. E. Partch, J. Org. Chem. 30, 2498 (1965).
K. Heusler, Helv. Chim. Ada 52, 1520 (1969).
M. Lj. Mihailović, M. Jakovljević, V. Trifunović, R. Vukov, and Ž. Čeković, Tetrahedron 24. 6959 (1968).
K. Heusler and J. Kalvoda, Helv. Chim. Acta 46, 2732 (1963).
K. Heusler and J. Kalvoda, Tetrahedron Lett. 1963, 1001.
K. Heusler, J. Kalvoda, G. Anner and A. Wettstein, Helv. Chim. Acta 46, 352 (1963).
R. O. C. Norman and R. A. Watson, J. Chem. Soc. (B) 1968. 184, 692.
W. H. Starnes Jr., J. Am. Chem. Soc. 90, 1807 (1968)
W. H. Starnes Jr., J. Org. Chem. 33, 2767 (1968).
K. Heusler Tetrahedron Lett. 1964, 3975.
M. Lj. Mihailović, M. Jakovljević, and Ž. Čeković, Tetrahedron 25. 2269 (1969).
K. Heusler, H. Labhart, and H. Loeliger, Tetrahedron Lett. 1965, 2847.
R. E. Partch and J. Monthony, Tetrahedron Lett. 1967, 4427.
M. Lj. Mihailović, Z. Maksimović, D. Jeremić, Ž. Čeković, A. Milovanović, and Lj. Lorenc, Tetrahedron 21. 1395 (1965).
G. B. Spero, J. L. Thompson, W. P. Schneider, and F. Kagan, J. Org. Chem. 28, 2225 (1963).
G. Bauslaugh, G. Jast, and E. Lee-Ruff, Canad. J. Chem. 44, 2837 (1966).
M. Lj. Mihailović, V. Andrejević, M. Jakovljević, D. Jeremić, A. Stojiljković, and R. E. Partch, Chem. Commun. 1970, 854.
G. Ohloff, K. H. Schulte-Elte, and B. Willhalm, Helv. Chim. Acta 49, 2135 (1966).
S. Forshull, C. Lagercrantz, and K. Torssell, Acta Chem. Scand. 23, 522 (1969).
C. Walling, Pure and Applied Chem. 15, 69 (1967).
Ch. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner, and A. Wettstein, Experientia 17, 475 (1961)
Ch. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner, and A. Wettstein, Helv. Chim. Acta 45, 1317 (1962).
R. H. Hesse, in Advances in Free Radical Chemistry, G. H. Williams, Ed., Vol. 3, pp. 83–137, Logos Press, London, 1969.
M. Akhtar, in Advances in Photochemistry. W. A. Noyes, G. S. Hammond, and J. N. Pitts, Eds., Vol.2, pp. 263–303, Interscience, New York, 1964.
H. Immer, M. Lj. Mihailović, K. SchaflFner, D. Arigoni, and O. Jeger, Experientia 16, 530 (1960);
H. Immer, M. Lj. Mihailović, K. Schaflher, D. Arigoni, and O. Jeger, Helv. Chim. Acta 45, 753 (1962).
M. Lj. Mihailović, Ž. Čeković, and D. Jeremić, Tetrahedron 21, 2813 (1965).
M. Lj. Mihailović, L. Živković, Z. Maksimović, D. Jeremić, Ž. Ceković, and R. Matić, Tetrahedron 23, 3095 (1967).
S. Moon and P. R. Clifford, J. Org. Chem. 32, 4017 (1967).
M. Lj. Mihailović, R. Matić, S. Orbović and Ž. Čeković, Bull. Soc. Chim. Beograd 36, 363 (1971).
S. Milosavljević, D. Jeremić and M. Lj. Mihailović, Tetrahedron 29, 3547 (1973).
M. Fisch, S. Smallcombe, J. C. Gramain, M. A. McKervea, and J. E. Anderson, J. Org. Chem. 35, 1886 (1970).
W. A. Aver, D. A. Law and K. Piers, Tetrahedron Lett. 1964, 2959.
D. Hauser, K. Schaflher and O. Jeger, Helv. Chim. Acta 47. 1883 (1964).
M. Lj. Mihailović, S. Konstantinović, A. Milovanović, K. Janković, Ž. Čeković, and D. Jeremić, Chem. Commun. 1969, 236.
M. Lj. Mihailović, G. Milosević, A. Milovanović, and Ž. Čeković, Bull. Sue. Chim. Beograd 43. 361 (1978).
D. Hauser, K. Heusler, J. Kalvoda, K. Schaflher, and O. Jeger, Helv. Chim. Acta 47, 1961 (1964).
M. Lj. Mihailović, Lj. Lorenć, and L Forsek, unpublished results.
K. Heusler, J. Kalvoda, Ch. Meystre, G. Anner, and A. Wettstein, Helv. Chim. Acta 45, 2161 (1962).
Ch. Meystre, J. Kalvoda, G. Anner, and A. Wettstein, Helv. Chim. Acta 46, 2844 (1963).
M. Lj. Mihailović, R. I. Mamuzić, Lj. Žigić-Mamuzić, J. Bosnjak, and Ž. Čeković, Tetrahedron 23, 215 (1967).
G. G. Abbot and F. D. Gunstone. Chem. Phys. Lipids 7, 303 (1971).
F D. Greene, M. L. Savitz, F. D. Osterholtz, H. H. Lau, W. N. Smith, and P. M. Zanet, J. Org. Chem. 28, 55 (1963).
M. Lj. Mihailović, Ž. Čeković, V. Andrejević, R. Matić, and D. Jeremić. Tetrahedron 24, 4947 (1968).
A. C. Cope, M. Gordon, S. Moon, and C. H. Park. J. Am. Chem. Soc. 87, 3119 (1965).
R. M. Moriarty and H. G. Walsh, Tetrahedron Lett. 1965, 465.
A. Cope, M. A. McKervey, N. M. Weinshenker, and R. B. Kinnel, J. Org. Chem. 35, 2918 (1970).
M. Lj. Mihailović et al., unpublished results.
S. G. Patnekar and S. C. Bhattacharyya, Tetrahedron 23, 919 (1967).
J. Lhomme and G. Ourisson, Chem. Commun. 1967, 436.
J. Lhomme and G. Ourisson, Tetrahedron 24, 3177 (1968).
Y. Shalon, Y. Yanuka, and S. Sarel, Tetrahedron Lett. 1969, 957.
A. S. Vaidya, S. M. Dixit, and A. S. Rao, Tetrahedron Lett. 1968, 5173.
S. Moon and B. H. Waxman, J. Org. Chem. 34, 288 (1969).
M. Lj. Mihailović and M. Miloradović, Tetrahedron 22. 723 (1966).
M. Lj. Mihailović, A. Milovanović, S. Konstantinović, J. Janković, Ž. Čeković, and R. E. Partch. Tetrahedron 25, 3205 (1969).
J. J. Partridge, N. K. Chadka, S. Faber, and M. Uskoković, Synth. Commun. 1, 233 (1971).
P. F. Beal and J. E. Pike, Chem. Ind. 1960, 1505.
U. Scheidegger, K. Schaflher, and O. Jeger, Helv. Chim. Acta 45, 400 (1962).
V.M. Mićović, S. Stojčić, M. Bralović, S. Mladenović, D. Jeremić, and M. Stefanović. Tetrahedron 25, 985 (1969).
S. Moon and L. Haynes, J. Org. Chem. 31, 3067 (1966).
M. Lj. Mihailović, Ž. Čeković, J. Stanković, N. Pavlović, S. Konstantinović, S. Djokić-Mazinjanin, and D. Marinković, Helv. Chim. Acta 56. 3056 (1973).
A. C. Cope, M. A. McKervey, and N. M. Weinshenker, J. Am. Chem. Soc. 89, 2932 (1967).
J. Kalvoda, Ch. Meystre, and G. Anner. Helv. Chim. Acta 49, 424 (1966).
J. Kalvoda, Helv. Chim. Acta 51, 267 (1968).
S. G. Patnekar, H. H. Mathur, and S. C. Bhattacharyya, Indian J. Chem. 4, 67 (1966); Chem. Ahstr. 64, 17643 (1966).
C. F. Seidel, D. Felix, A. Eschenmoser, K. Biemann, E. Palluy, and M. Stoll, Helv. Chim. Acta 44. 598 (1961).
R. L. Markus, U.S. Patent No. 3,166,576 (1965); Chem. Ahstr. 62, 11785 (1965).
M. Lj. Mihailović, G. Milosević, and A. Milovanović, Tetrahedron 34, 2587 (1978).
M. Lj. Mihailović, S. Konstantinović, and S. Djokić-Mazinjanin, Bull. Soc. Chim. Beograd 41, 281 (1976).
K. Kitahonoki and A. Matsuura, Tetrahedron Lett. 1964, 2263.
J. Bosnjak, V. Andrejević, Ž. Čeković, and M. Lj. Mihailović, Tetrahedron 28. 6031 (1972).
M. Lj. Mihailović and S. Milosavljević, unpublished results.
P. Brun and B. Waegell, Bull. Soc. Chim. France 1972, 1825.
P. Brun, M. Pally, and B. Waegell, Tetrahedron Lett. 1970, 331.
F. Kuong-Huu, C. R. Bennett, P. E. Fouche, and R. Goutarel, C. R. Acad. Sci. Paris Ser. C 275, 499 (1972).
M. Lj. Mihailović, J. Bosnjak, and Ž. Čeković, Helv. Chim. Acta 57, 1015 (1974).
J. Bukhard, J. Janku, and S. Landa, Coll. Czech. Chem. Commun. 39, 1072 (1974).
M. A. McKervey, Chem. Ind. 1967, 1791.
W. H. W. Lunn, W. D. Podmore and S. S. Szinai, J. Chem. Soc. (C) 1968, 1657.
G. Eadon, J. Am. Chem. Soc. 98, 7313 (1976).
M. P. Zink, J. Ehrenfreund, and H. R. Wolf. Helv. Chim. Acta 57, 1116 (1974).
P. Brun and B. Waegell. Tetrahedron 32. 1197 (1976).
K. Heusler, J. Kalvoda, P. Wieland, G. Anner, and A. Wettstein. Helv. Chim. Acta 45, 2575 (1962).
C. W. Shoppe, J. C. Call, and R. E. Lack, J. Chem. Soc. (C) 1970, 1893.
P. Narasimha Rao and J. C. Uroda, Naturwissenschaften 50. 548 (1963).
M. E. Wolff, W. Hoo, and R. Kwok, Steroids 5, 1 (1969).
R. Kwok and M. E. Wolff. J. Org. Chem. 28, 423 (1963).
H. Mori, K. Shibata, R. Ouchi, and N. Yamakoshi, Japan Kokai 74 30,366; Chem. Abstr. 81, 49921 (1974).
P. Morand and A. Polakova-Paquet, Canad. J. Chem. 51, 4098 (1973).
K. Heusler. Chimia 21, 557 (1967).
A. Bowers, E. Denot, L. C. Ibanez, M. L. Cabezas, and H. J. Ringold, J. Org. Chem. 27, 1862 (1962).
A. Bowers, L. C. Ibanez, M. L. Cabezas, and H. J. Ringold, Chem. Ind. 1960, 1299.
J. F. Bagli, P. F. Morand, and R. Gaudry, J. Org. Chem. 28, 1207 (1963).
X. Lusinchi and G. Robolt, Bull. Soc. Chim. France 1967, 3498.
A. Bowers, R. Villotti, J. Edwards, E. Denot, and O. Halpern, J. Am. Chem. Soc. 84, 3204 (1962).
B. Berkoz, E. Denot, and A. Bowers, Steroids 1, 251 (1963).
J. Kalvoda and K. Heusler, Chem. Ind. 1963, 1431.
P. B. Sollman, J. Org. Chem. 28, 3559 (1963).
R. M. Moriarty and T. D. D’Silva, J. Org. Chem. 28, 2445 (1963).
J. Tadanier, J. Org. Chem. 28, 1744 (1963).
K. Tanabe, R. Takasaki, K. Sakai, R. Hayashi, and Y. Morisawa, Chem. Pharm. Bull. (Tokyo) 10, 1126 (1962).
J. C. Knight, J. L. Belletne, and G. R. Pettit. J. Chem. Soc. (C) 1967. 2427.
J. T. Bentley, R. B. Boar, R. W. Draper, J. F. McGhie, and D. H. R. Barton, J. Chem. Soc. Perkin Trans. I 1972, 749.
C. W. Shoppee, N. W. Hughes, and R. E. Lack, J. Chem. Soc. (C) 1966, 2359.
J. Fried, J. W. Brown, and L. Brokenhagen, Tetrahedron Leu. 1965, 2499.
L. Kohout, Coll. Czech. Chem. Commun. 37, 2227 (1972).
J. Kalvoda, G. Anner, D. Arigoni, K. Heusler, H. Immer, O. Jeger, M. Lj. Mihailović, K. Schaffner, and A. Wettstein, Helv. Chim. Acta 44, 186 (1961).
Ch. R. Engel and G. J. Beaudouin, Tetrahedron Lett. 1968, 1887.
G. Cainelli, B. Kamber, J. Keller, M. Lj. Mihailović, D. Arigoni, and O. Jeger, Helv. Chim. Acta 44, 518 (1961).
T. Koga and M. Tomoeda, Tetrahedron 26, 1043 (1970).
M. Tomoeda and T. Koga, Tetrahedron Lett. 1965, 3231.
A. Bowers and E. Denot, J. Am. Chem. Soc. 82, 4956 (1960).
I. G. Guest, J. G. L. Jones, B. A. Marples, and M. J. Harrington, J. Chem. Soc. (C) 1969, 2360.
M. J. Harrington and B. A. Marples, Chem. Ind. 1968, 484.
J. G. L. Jones and B. A. Marples, J. Chem. Soc. Perkin Trans. I 1973, 1143.
K. Heusler and J. Kalvoda, Helv. Chim. Acta 46, 2020 (1963).
L. Velluz, G. Muller, R. Bardoneschi, and A. Poittevin, C. R. Acad. Sci. Paris 250, 725 (1960).
P. F. Beal and J. E. Pike, Chem. Ind. 1960, 1505.
S. Moon and J. M. Lodge, J. Org. Chem. 29, 3453 (1964).
R. M. Moriarty and K. Kapadia, Tetrahedron Lett. 1964, 1165.
C. Ehret and G. Ourisson, Bull. Soc. Chim. France 1968, 2629.
T. Okuda and T. Yoshida, Chem. Ind. 1965, 37.
Y. Watanabe, Y. Mazuhara, and M. Shiota, Chem. Commun. 1969, 984.
M. Lj. Mihailović, Ž. Čeković, J. Stanković, S. Djokic-Mazinjanin, D. Marinković, and S. Kon-stantinović. Bull. Soc. Chim. Beograd 43, 69 (1978).
M. Lj. Mihailović. S. Konstantinović, and Ž. Čeković, unpublished results.
M.-P. Bertrand, J.-M. Surzur, M. Boyer and M. Lj. Mihailović, Tetrahedron 35, 1365 (1979).
J. Ehrenfreund, M. P. Zink and H. R. Wolf, Helv. Chim. Acta 57, 1098 (1974).
C. Walling and A. Padwa, J. Am. Chem. Soc. 85, 1593, 1597 (1963).
C. Walling and P. J. Wagner, J. Am. Chem. Soc. 86, 3368 (1964).
M. Lj. Mihailović and Ž. Čeković, Helv. Chim. Acta 52, 1146 (1969).
J. Lhomme and G. Ourisson, Tetrahedron 24, 3167 (1968).
M. Amorosa, L. Caglioti, G. Cainelli, H. Immer, J. Keller, H. Wehrli, M. Lj. Mihailović, K. Schaffner, D. Arigoni and O. Jeger, Helv. Chim. Acta 45, 2674 (1962).
M. Stefanović, M. Gasic, Lj. Lorenc, and M. Lj. Mihailović, Tetrahedron 20, 2289 (1964).
W. A. Mosher, C. L. Kehr, and L. W. Wright, J. Org. Chem. 26. 1044 (1961).
G. Wolff and G. Ourisson, Tetrahedron 25, 4903 (1969).
H. Wehrli, M. S. Heller, K. Schaffner, and O. Jeger, Helv. Chim. Acta 44. 2162 (1961).
J. Iriarte, K. Schaffner, and O. Jeger, Helv. Chim. Acta 1599 (1963).
M. Lj. Mihailović, M. Stefanović, Lj. Lorenc, and M. Gašić, Tetrahedron Lett. 1964, 1867.
M. Lj. Mihailović, Lj. Lorenc, M. Gašić, M. Rogić, A. Melera, and M. Stefanović, Tetrahedron 22. 2345 (1966).
D. Rosenthal, C. E. Lefiler, and M. E. Wall, Tetrahedron Lett. 1965, 3203.
D. Rosenthal, C. F. Leffler, and M. E. Wall, Tetrahedron 23, 3583 (1967).
M. Lj. Mihailović, Lj. Lorenc, V. Pavlović, M. Dabović and G. Pavlović, Bull. Soc. Chim. Beograd 46, 235 (1981).
V. M. Micović and M. Lj. Mihailović, Rec. Trav. Chim. Pays-Bas 71, 970 (1952).
R. E. Partch, Tetrahedron Leu. 1964, 3071.
H. Oberwasser, K. Heusler, J. Kalvoda, Ch. Meystre, P. Wieland, G. Anner, and A. Wettstein. Helv. Chim. Acta 46. 344 (1963).
R. Criegee, Ber. Dtsch. Chem. Ges. 64, 260 (1931).
A. S. Perlin, in Oxidation, R. L. Augustine. Ed., Vol. 1, pp. 189, Marcel Dekker, New York, 1969.
R. Criegee and E. Biichner, Ber. Dtsch. Chem. Ges. 73, 563 (1940).
R. Criegee, C. Kraft, and B. Rank, Ann. Chem. 507, 159 (1933).
E. Baer, J. Am. Chem. Soc. 62, 1597 (1940); 64, 1416 (1942).
C. A. Bunton and M. D. Carr, J. Chem. Soc. 1963, 770.
R. Criegee, E. Hoger, G. Huber, P. Kruck, F. Marktscheffel, and H. Schellenberger, Ann. Chem. 599, 81 (1956).
H. R. Goldschmidt and A. S. Perlin, Canad. J. Chem. 38. 2280 (1960).
C. A. Grob and P. W. Schicss, Helv. Chim. Acta 43, 1546 (1960).
R. P. Bell, V. G. Rivlin, and W. A. Waters, J. Chem. Soc. 1958, 1696.
R. Criegee, E. Buchner, and W. Walther, Ber. Dtsch. Chem. Ges. 73, 571 (1940).
E. J. Moriconi, F. T. Wallenberger, and W. F. O’Connor, J. Am. Chem. Soc. 80, 656 (1958).
S. J. Angyal and R. J. Young, J. Am. Chem. Soc. 81, 5467 (1959).
R. Criegee, B. Marchand, and H. Winnowius, Ann. Chem. 550, 99 (1942).
K. Alder and H. A. Dortmann, Chem. Ber. 87, 1905 (1954).
L. P. Kuhn, J. Am. Chem. Soc. 76, 4323 (1954).
V. Prelog, K. Schenker, and W. Kung, Helv. Chim. Acta 36, 471 (1953).
V. Prelog, K. Schenker, and H. H. Gunthard, Helv. Chim. Acta 35, 1598 (1952).
W. S. Trahanovsky, J. R. Gilmore, and P. C. Heaton, J. Org. Chem. 38. 760 (1973).
J. P. Cordner and K. H. Pausacker, J. Chem. Soc. 1953, 102.
J. W. Clark-Lewis and L. R. Williams, Austral. J. Chem. 16, 869 (1963).
H. F. Bauer and D. E. Stuetz. J. Am. Chem. Soc. 78, 4097 (1956).
C. T. Bishop, Methods Carbohydrate Chem. 6, 350 (1972).
P. S. O’Colla, Methods Carbohydrate Chem. 5, 382 (1965).
S. Suzuki, Kagaku No Ryoika 17, 449 (1963); Chem. Abstr. 59, 14093e (1963).
R. Criegee, Ann. Chem. 495. 211 (1932).
R. C. Hockett, M. T. Dienes, and H. E. Ramsden, J. Am. Chem. Soc. 65, 1474 (1943).
A. C. Perlin and C. Brice, Can. J. Chem. 34, 541 (1956).
R. C. Hockett and M. Zief, J. Am. Chem. Soc. 72, 2130 (1950).
K. Matsuzaki, K. Sato, K. Ishii, M. Moriya, and H. Sobue. Kogyo Kagaku Zasshi 62, 1227 (1959); Chem. Abstr. 57, 15392 (1959).
J. D. Roberts and S. W. Sauer, J. Am. Chem. Soc. 71, 3925 (1949).
M. Nakajima, I. Tomida and S. Takei, Chem. Ber. 92, 163 (1959).
G. W. K. Cavill and D. H. Solomon, Austral. J. Chem. 13, 121 (1960).
K. Alder and H. Wirtz, Ann. Chem. 601, 138 (1956).
E. Vogel, Chem. Ber. 85, 25 (1952).
P. Karrer and R. Hirohata, Helv. Chim. Acta 16, 959 (1933).
L. Vargha and M. Remenyi, J. Chem. Soc. 1951, 1068.
E. L. Eliel and C. Pillar, J. Am. Chem. Soc. 77, 3600 (1955).
G. L. Buchanan, J. G. Hamilton, and R. A. Raphael, J. Chem. Soc. 1963, 4606.
A. W. Burgstahler and M. O. Abdel-Rahman, J. Am. Chem. Soc. 85. 173 (1963).
J. K. Stille and R. T. Foster, J. Org. Chem. 28, 2703 (1963).
J. T. Scanlan and D. Swern. J. Am. Chem. Soc. 62, 2305 (1940).
J. T. Scanlan and D. Swern. J. Am. Chem. Soc. 62. 2309 (1940).
F. Bouquet and C. Paquet. Bull. Soc. Chim. France 1949. 440.
P. Tomboulian. J. Org. Chem. 26, 2652 (1961).
H. Setter and E. Rauscher. Chem. Ber. 93. 1161 (1960).
A. D. Cross, E. Dcnot, R. Acevedo, R. Urquiza and A. Bowers. J. Org. Chem. 29. 2195 (1964).
H. Schmid and K. Kagi, Helv, Chim. Acta 33, 1582 (1950).
G. Lardelli and O. Jeger, Helv. Chim. Acta 32. 1817 (1949).
J. M Grosheintz. J. Am. Chem. Sac. 61, 3379 (1939).
G. Rembarz, Chem. Ber. 95. 1565 (1962).
A. S. Perlin and C. Brice, Canad. J. Chem. 34, 85 (1956).
P. Karrer and K. Pfaehler, Helv, Chim. Acta 17, 363 (1934).
W. S. McClenahan and R. C. Hockett, J. Am. Chem. Soc. 60, 2061 (1938).
J. Fried and D. E. Walz, J. Am. Chem. Soc. 14, 5468 (1952).
V. Zitko and C. T. Bishop, Canad. J. Chem. 44, 1749 (1966).
P. J. Garratt and K. P. Vollhardt. Synthesis, 423 (1971).
K. T. Potts and R. Robinson, J. Chem. Soc. 1955, 2675.
F. Wessely and F. Sinwel, Monatsh. Chem. 81, 1055 (1950).
F. Wessely, J. Kotlan and W. Metlesics, Monatsh. Chem. 85, 69 (1954).
F. Wessely, E. Zbiral, and J. Jorg, Monatsh. Chem. 94, 227 (1963).
F. Wessely, E. Zbiral and H. Sturm. Monatsh. Chem. 93, 15 (1962).
F. Wessely, J. Swoboda, and V. Guth, Monatsh. Chem. 95, 649 (1964).
F. Wessely, J. Kotlan and F. Sinwel. Monatsh. Chem. 83. 902 (1952).
F. Wessely, E. Zbiral and H. Sturm, Chem. Ber. 93, 2840 (1960).
E. Zbiral, F. Wessely, and J. Jorg, Monatsh. Chem. 92. 654 (1961).
G. W. K. Cavill, E. R. Cole, R. T. Gilham, and D. J. McHugh, J. Chem. Soc. 1954. 2785.
G. N. Bogdanov, M. S. Postnikova, and N. M. Emanuel, lzv. Akad. Nauk SSSR Old. Khim. Nauk 1963. 173.
F. R. Hewgill and D. G. Hewitt. J. Chem. Soc. (C) 1967, 723, 726.
F. R. Hewgill and B. S. Middleton, J. Chem. Soc. (C) 1967, 2316.
F. R. Hewgill and S. L. Lee, J. Chem. Soc. (C) 1968, 1556.
E. Hecker and P. Lattrell, Ann. Chem. 662, 48 (1963).
M. J. Harrison and R. O. C. Norman, J. Chem. Soc. (C) 1970, 728.
F. Takacs, Monatsh. Chem. 95, 961 (1964).
F. Wessely, G. Lauterbach-Kcil, and F. Sinwel, Monatsh. Chem. 81, 811 (1950).
O. Dimroth, O. Friedemann, and H. Kammerer, Ber. Dtsch. Chem. Ges. 53, 481 (1920).
K. H. Konig, W. Schulze, and G. Moller, Chem. Ber. 93, 554 (1960).
W. Metlesics, E. Schinzel, H. Vilcsek, and F. Wessely, Monatsh. Chem. 88, 1069 (1957).
F. Wessely and E. Schinzel, Monatsh. Chem. 84, 425 (1953).
F. Wessely and J. Kotlan, Monatsh. Chem. 84, 291 (1953).
K. Ichikawa and Y. Yamaguchi. J. Chem. Soc. Jpn 73, 415 (1952).
E. W. Garbisch, Jr., J. Org. Chem. 30, 2109 (1965).
H. Musso. Angew. Chem. 75, 965 (1963).
H. B. Henbest, D. N. Jones and G. P. Later, J. Chem. Soc. 1961, 4472.
J. D. Cocker, H. B. Henbest, G. H. Phillips, G. P. Slater, and D. A. Thomas, J. Chem. Soc. 1965, 6.
S. Moon and H. Bohm. J. Org. Chem. 37, 4338 (1972).
M. Lj. Mihailović, D. Jeremic, Ž. Čeković, J. Bosnjak and V. Andrejević. Bull. Soc. Chim. Beograd 41, 17 (1976).
E. Detilleux and J. Jadot, Bull. Soc. R. Sci. Liege 29, 208 (1960).
O. Dimroth and R. Schweizer, Ber. Dtsch. Chem. Ges. 56, 1375 (1923).
G. W. K. Cavill and D. H. Solomon, J. Chem. Soc. 1955, 4426.
J. W. Ellis, J. Org. Chem. 34. 1154 (1969).
M. Lj. Mihailović, J. Forsek, and Lj. Lorenc. J. Chem. Soc. Perkin Trans. I 1982. 1.
M. Stefanović, Z. Djarmati, and M. Gašić. Tetrahedron Lett. 1970, 2769; Bull. Soc. Chim. Beograd 37, 373 (1972).
O. Polansky, E. Schinzel, and P. Wessely, Monatsh. Chem. 87, 24 (1956).
G. W. K. Cavill, A. Robertson, and W. B. Whalley, J. Chem. Soc. 1949, 1567.
R. Criegee and K. Klonk, Ann. Chem. 564. 1 (1949).
W. Treibs and P. Grossmann. Chem. Ber. 90. 103 (1957).
G. W. K. Cavill, D. L. Ford, H. Hinterberger, and D. H. Solomon. Austral. J. Chem. 13, 121 (1960).
J. Y. Satoh et al,. Bull. Chem. Soc. Jpn 46. 3155 (1973).
L. F. Fieser and R. Stevenson, J. Am. Chem. Soc. 76, 1728 (1954).
L. F. Fieser and M. A. Romero, J. Am. Chem. Soc. 75, 4716 (1953).
F. Sondheimer, S. Kaufmann, J. Romo, H. Martinez, and G. Rosenkranz. J. Am. Chem. Soc. 75, 4712 (1953).
A. D. Boul, R. Macrae, and G. D. Meakins, J. Chem. Soc. Perkin Trans. I 1974, 1138.
T. Reichstein and C. Montigei, Helv. Chim. Acta 22, 1212 (1939).
J. K. Kochi, J. D. Bacha, and T. W. Bethea, J. Am. Chem. Soc. 89, 6538 (1967).
J. K. Kochi, J. Am. Chem. Soc. 87, 1811 (1965)
ibid. 87, 3609 (1965).
D. I. Davies and G Waring, J. Chem. Soc. (C) 1968, 1865, 2332.
J. K. Kochi and J. D. Bacha, J. Org. Chem. 33, 2746 (1968).
H. Loeliger, Helv. Chim. Acta 52, 1516 (1969).
E. J. Corey and J. Casanova, J. Am. Chem. Soc. 85, 165 (1963).
M. Julia, F. LeGoflk, and L. Katz, Bull. Soc. Chim. France 1964, 1122.
J. D. Bacha and J. K. Kochi, J. Org. Chem. 33, 83 (1968).
J. K. Kochi, A. Bemis, and C. L. Jenkins, J. Am. Chem. Soc. 90, 4616 (1968).
C. L. Jenkins and J. K. Kochi, J. Am. Chem. Soc. 94, 843 (1972).
J. D. Bacha and J. K. Kochi, Tetrahedron 24, 2215 (1968).
J. K. Kochi, J. Am. Chem. Soc. 87, 2500 (1965)
J. Org. Chem. 30, 3265 (1965).
C. L. Jenkins and J. K. Kochi, J. Org. Chem. 36, 3095 (1971).
R. D. Stolow and T. W. Giants, Tetrahedron Lett. 1971, 3095.
M. Lj. Mihailović, J. Bosnjak, and Ž. Čeković, Helv. Chim. Acta 57, 1015 (1974).
D. H. R. Barton, H. P. Faro, E. P. Serebryakov, and N. F. Woolsey, J. Chem. Soc. 1965, 2438.
U. Scheidegger, J. E. Baldwin, and J. D. Roberts, J. Am. Chem. Soc. 89, 894 (1967).
G. B. Bachman and J. W. Wittmann, J. Org. Chem. 28, 65 (1963).
C. A. Grob, M. Ohta, and A. Weiss, Angew. Chem. 70, 343 (1958)
C. A. Grob, M. Ohta, E. Renk, and A. Weiss, Helv. Chim. Acta 41, 1191 (1958).
C. A. Grob and A. Weiss, Helv. Chim. Acta 43, 1390 (1960).
N. B. Chapman, S. Sotheeswaren, and J. K. Toyne, Chem. Commun. 1965, 214; J. Org. Chem. 35, 917 (1970).
E. E. van Tamelen and S. P. Pappas, J. Am. Chem. Soc. 85, 3297 (1963).
C. M. Cimarusti and J. Wolinsky, J. Am. Chem. Soc. 90, 113 (1968).
L. L. McCoy and A. Zagalo, J. Org. Chem. 25, 284 (1960).
J. J. Tufariello and W. J. Kissel, Tetrahedron Lett. 1960, 6145.
J. Meinwald, J. J. Tufariello, and J. J. Hurst, J. Org. Chem. 29, 2914 (1964).
K. Shirahata, T. Kato, Y. Kitahara, and N. Abe, Tetrahedron 25, 3179 (1969).
H. Musso, K. Naumann, and K. Grychtol, Chem. Ber. 100, 3614 (1967).
R. M. Moriarty, H. G. Walsh, and H. Gopal, Tetrahedron Lett. 1966, 4363.
R. M. Moriarty, H. Gopal, and H. G. Walsh, Tetrahedron Lett. 1966, 4369.
M. Lj. Mihailović, J. Bosnjak, and Ž. Čeković, Helv. Chim. Acta 59, 475 (1976).
G. Btichi, R. E. Erickson, and N. Wokabayeshi, J. Am. Chem. Soc. 83, 927 (1961).
C. R. Bennett, R. C. Cambie, and W. A. Denny, Austr. J. Chem. 22, 1069 (1969).
N. P. Jensen and W. S. Johnson, J. Org. Chem. 32, 2045 (1967).
A. S. Vaidya, S. M. Dixit, and A. S. Rao, Tetrahedron Lett. 1968, 5173.
D. L. Struble, A. L. J. Beckwith, and G. E. Gream, Tetrahedron Lett. 1970, 4795.
A. C. Cope, C H. Park, and P. Scheiner, J. Am. Chem. Soc. 84, 4862 (1962).
W. A. Mosher and C. L. Kehr, J. Am. Chem. Soc. 75, 3172 (1953).
M. Julia and F. LeGoflic, Bull. Soc. Chim. France 1965, 1555.
L. Birladeaun, T. Hanafusa, and S. Winstein, J. Am. Chem. Soc. 88, 2315 (1966).
A. L. J. Beckwith, R. T. Cross, and G. E. Gream, Austral. J. Chem. 27, 1673 (1974).
T. Nozoe, T. Asao, M. Ando, and K. Takase, Tetrahedron Lett. 1967, 2821.
H. Christol, D. Moers, and T. Pietrasanta, Bull. Soc. Chim. France 1969, 962.
D. H. R. Barton and E. P. Serebryakov, Proc. Chem. Soc. 1962, 309.
T. Shono, I. Nishiguchi, and R. Oda, Tetrahedron Lett. 1970, 373.
R. N. McDonald and L. E. Reineke, J. Am. Chem. Soc. 87, 3020 (1965).
S. Masamune, E. N. Cain, R. Vukov, S. Takada, and N. Nakatsuka, Chem. Commun. 1969, 243.
G. P. Kugatova-Shemyakina and V. B. Berzins, Zh. Org. Khim. SSSR 7, 2292 (1971); Chem. Abstr. 76, 45797 (1972).
J. Kazan and F. D. Greene, J. Org. Chem. 28, 2965 (1963).
J. B. Hendrickson and R. K. Boeckmann, J. Org. Chem. 36, 2315 (1971).
W. G. Dauben, G. M. Schallhorn, and D. L. Whalen, J. Am. Chem. Soc. 93, 1446 (1971).
D. I. Davis and C. Waring, Chem. Commun. 1965, 263.
D. I. Davis and C. Waring. J. Chem. Soc. (C) 1967, 1639.
M. Lj. Mihailović, A. Stojiljković and V. Andrejević. Tetrahedron Lett. 1965. 461.
A. Stojiljković, V. Andrejević, and M. Lj. Mihailović. Tetrahedron 23. 721 (1967).
H. E. Baumgarten, D. F. McLaeu and H. W. Taylor, J. Org. Chem. 36. 3668 (1971).
K. N. Parameswaren and O. M. Friedman, Chem. Ind. 1965, 988.
A. J. Sisti, Chem. Commun. 1968, 1272.
A. J. Sisti and S. R. Milstein, J. Org. Chem. 39, 3932 (1974).
K. H. Pausacker and J. G. Scroggie, J. Chem. Soc. 1954, 4003.
K. Dimroth, F. Kalk, and G. Neubauer, Chem. Ber. 90, 2058 (1957).
H. J. Richter and R. L. Dressier, J. Org. Chem. 27, 4066 (1962).
R. W. Hoffman and K. R. Eicken, Chem. Ber. 100, 1465 (1967).
H. Milne and G F. Frost, J. Org. Chem. 33, 169 (1968).
K. Nakagawa and H. Onoue, Chem. Commun. 1965, 396.
L. Horner, E. Winkelmann, K. H. Knopp, and W. Ludwig, Chem. Ber. 92, 288 (1959).
B. Acott and A. L. J. Beckwith, Chem. Commun. 1965, 161.
H. E. Baumgarten, H. L. Smith, and A. Staklis, J. Org. Chem. 40, 3554 (1975).
B. Acott, A. L. J. Beckwith, and A. Hassanali, Austral. J. Chem. 21, 197 (1968)
21, 185 (1968).
D. H. R. Barton and A. L. J. Beckwith, Proc. Chem. Soc. 1963, 335.
D. H. R. Barton, A. L. J. Beckwith, and A. Goosen, J. Chem. Soc. 1965, 181.
J. B. Aylward, J. Chem. Soc. (C) 1969, 1633.
G. Koga and J.-P. Anselme, J. Am. Chem. Soc. 91, 4323 (1969).
R. W. Hoffman. Chem. Ber. 97, 2763, 2772 (1964).
R. A. Clement. J. Org. Chem. 25, 1724 (1960).
H. Kropf and R. Lambeck. Ann. Chem. 700, 1, 18 (1966).
D. C. inland and D. X. Cnner, Chem. Ind. 1956, 176.
S. Kaufman, L. Tokes, J. W. Murphy, and P. Crabbe, J. Org. Chem. 34, 1618 (1969).
G. Just and K. Dahl, Tetrahedron Lett. 1966, 2441.
A. Battaglia, A. Dondoni, and A. Mangini, J. Chem. Soc. B 1971, 554.
H. Kropf, Angew. Chem. Int. Ed. 4, 1091 (1965).
Y. Yukawa, M. Sakai and S. Suzuki, Bull. Chem. Soc. Jpn 39, 2266 (1966).
A. Stojiljković, N. Orbović, S. Sredojević, and M. Lj. Mihailović, Tetrahedron 26. 1101 (1970).
D. H. R. Barton, J. F. McGhie, and P. L. Batten, J. Chem. Soc. C 1970, 1033.
D. M. Gale, W. J. Middleton, and C. G. Krespan, J. Am. Chem. Soc. 88, 3617 (1966).
E. Ciganek, J. Org. Chem. 30, 4193 (1965).
W. A. F. Gladstone, J. B. Aylward, and R. O. C. Norman, J. Chem. Soc. C 1969, 2587.
R. N. Butler and F. L. Scott, J. Chem. Soc. C 1966, 1202.
T. Saski and K. Kanematsu, J. Chem. Soc. C 1971, 2147.
R. N. Butler and W. B. King, J. Chem. Soc. Perkin Trans. I 1975, 61.
D. C. Iflland, L. Salisbury and W. R. Schafer, J. Am. Chem. Soc. 83, 747 (1961).
M. J. Harrison, R. O. C. Norman, and W. A. F. Gladstone. J. Chem. Soc. C 1967, 735.
J. Buckingham and R. D. Guthrie, J. Chem. Soc. C 1968, 1445.
W. A. F. Gladstone and R. O. C. Norman, J. Chem. Soc. 1965. 3048. 5177.
W. A. F. Gladstone and R. O. C. Norman, J. Chem. Soc. C 1966, 1536.
H. Kropf and H. von Wallis, Synthesis, 1981, 237, 633.
K. Alder and S. Schneider, Liebigs Ann. Chem. 524, 189 (1936).
R. Criegee, H. Kristinsson, D. Seebach and F. Zanker, Chem. Ber. 98, 2331 (1965).
E. J. Corey and H. L. Pearce, J. Am. Chem. Soc. 101, 5841 (1979).
E. J. Corey and A. W. Gross, Tetrahedron Lett. 1980, 1819.
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© 1986 Plenum Press, New York
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Mihailović, M.L., Čeković, Ž., Lorenc, L. (1986). Oxidations with Lead Tetraacetate. In: Mijs, W.J., de Jonge, C.R.H.I. (eds) Organic Syntheses by Oxidation with Metal Compounds. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2109-5_14
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