Abstract
The chemistry of adamantane and related “cage-like” hydrocarbons has developed rapidly in recent years. These developments, encompassing a broad spectrum of the chemical world, have not been stimulated by any unique properties associated with the cage strutures of these molecules; the chemistry of such systems is typically hydrocarbon in nature. The particular utility of “cage-like” substrates in a variety of chemical investigations arises, for the most part, from their conformational rigidity; variables (e.g. those associated with structure) appropriate to more mobile compounds are often eliminated by the use of “cage-like” systems. The availability, ease of functionalization, and the near ideal structure of adamantane make it extremely useful for this purpose.
National Institutes of Health Predoctoral Fellow, 1968–1970.
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Landa, S.: Chem. Listy 27, 415, 443 (1933).
Schleyer, P. von R.: J. Am. Chem. Soc. 79, 3292 (1957).
-, Donaldson, M. M.: J. Am. Chem. Soc. 82, 4645 (1960).
Fort, R. C., Schleyer, P. von R.: Chem. Rev. 64, 277 (1964).
The literature has been surveyed through June, 1970. Some of the more recent literature (through Jan. 1971) is included in the form of an addendum at the end of this article. Heterocyclic adamantanes have generally not been included. Recent reciews of this field are available 6).
Gelbard, G.: Ann. Chim. (Paris) 4, 331 (1969); Bernaert, E.: Ind. Chim. Belge. 35, 715 (1970);-Sevost'yanova, U. V., Krayushkin, M. M., Yurchenko, A. G.: Usp. Khim. 39, 1721 (1970).
Friedel, C., Gorgeu, A.: Compt. Rend. 127, 590 (1898).
Pines, H., Hoffmann, N. E.: Friedel-Crafts and Related Reactions, Vol. II, Part 2, Ch. 28, G. A. Olah, Ed. New York: Interscience Publishers 1964.
Landa, S., Hala, S.: Chem. Listy 51, 2325 (1957).
--: Collection Czech. Chem. Commun. 24, 93 (1959).
Ault, A., Kopet, R.: J. Chem. Educ. 46, 612 (1969).
Schleyer, P. von R., Nicholas, R. D.: Tetrahedron Letters 305 (1961).
Schneider, A., Warren, R. W., Janoski, E. J.: J. Am. Chem. Soc. 86, 5365 (1964).
---: J. Org. Chem. 31, 1617 (1966).
---: Trans. N. Y. Acad. Sci. Ser. II., 30, 3 (1967).
Pines, H., Abraham, B. M., Ipatieff, V. N.: J. Am. Chem. Soc. 70, 1742 (1948).
For a review see Ref. 6).
Schneider, A.: U. S. Patent 3, 128, 316, April 7, 1964; cf. Chem. Abstr. 61, 4244a (1964).
-: Neth. Patent Appl. 300, 223, Sept. 10, 1965; cf. Chem. Abstr. 64, 6528 (1966).
Williams, V. Z. Jr.: A. B. Thesis, Princeton University (1965).
Robinson, M. J. T., Tarratt, H. J. F.: Tetrahedron Letters 5 (1968).
Hoffmann, H., Trottier, C. H.: U. S. Patent 3, 457, 317, July 22, 1969; cf. Chem. Abstr. 71, 90942 (1969).
Blanchard, K. B.: Ph. D. Thesis, Princeton University (1967); cf. Bagrii, E. I., Frid, T. Yu., Sanin, P. I.: Neftekhimiya, 10, 480 (1970); Chem. Abstr., 13, 109130 (1970).
Hala, S., Landa, S.: Collection Czech. Chem. Commun. 29, 1319 (1964).
Schleyer, P. von R., Gleicher, G. J., Cupas, C. A.: J. Org. Chem. 31, 2014 (1966).
Goscin, S. A.: A. B. Thesis, Princeton University (1966).
Nonura, M., Schleyer, P. von R., Arz, A. A.: J. Am. Chem. Soc. 89, 3657 (1967).
Vogl, O., Anderson, B. C., Simons, D. M.: Tetrahedron Letters 415 (1966).
Cupas, C., Schleyer, P. von R., Trecker, D. J.: J. Am. Chem. Soc. 87, 917 (1965).
Karle, I. L., Karle, J.: J. Am. Chem. Soc. 87, 919 (1965).
Gund, T. M., Williams, V.Z., Jr., Osawa, E., Schleyer, P. v. R.: Tetrahedron Letters 3877 (1970).
Goscin, S. A.: unpublished results.
Williams, V. Z., Jr., Schleyer, P. von R., Gleicher, G. J., Rodewald, L. B.: J. Am. Chem. Soc. 88, 3862 (1966).
Carrell, H. L., Donohue, J.: Tetrahedron Letters 3503 (1969).
Schleyer, P. von R., Osawa, E., Drew, M. G. B.: J. Am. Chem. Soc. 90, 5034 (1968).
-Wiskott, E.: Tetrahedron Letters 2845 (1967).
Hala, S., Landa, S.: Angew. Chem. 78, 1060 (1966).
Wiskott, E.: unpublished results. Landa, S.: unpublished results
Kent, G. J.: unpublished results.
Osawa, E.: unpublished results.
Rao, S. T., Sundaralingam, M., Osawa, E., Wiskott, E., Schleyer, P. v. R.: Chem. Commun. 861 (1970).
Olah, G. A.: private communication.
Balaban, A. T., Farcasiu, D., Bania, R.: Rev. Roumaine Chem. 11, 1205 (1966).
Whitlock, H. W., Jr., Siefken, M. W.: J. Am. Chem. Soc. 90, 4929 (1968).
Paquette, L. A., Meehan, G. V., Marshall, S. J.: J. Am. Chem. Soc. 91, 6779 (1969).
Lenoir, D., Schleyer, P. v. R.: Chem. Commun. 941 (1970).
Corey, E. J., Glass, R. S.: J. Am. Chem. Soc. 89, 2600 (1967).
Cash, D. J., Wilder, P. Jr.: Tetrahedron Letters 6445 (1966).
Karabatsos, G. J., Vane, F. M.: J. Am. Chem. Soc. 85, 729 (1963).
Majerski, Z., Wolf, A.P., Schleyer, P. v. R.: J. Labelled Cpds. 6, 179 (1970).
-, Schleyer, P. v. R., Wolf, A. P.: J. Am. Chem. Soc. 92, 5731 (1970).
Liggero, S.H., Majerski, Z., Schleyer, P. v. R., Wolf, A. P., Wynberg, H.: J. Labelled Cpds. in press.
Majerski, Z., Liggero, S. H., Schleyer, P. v. R., Wolf, A. P.: Chem. Commun., 1596 (1970).
Schleyer, P. v. R., Fort, R. C., Jr., Watts, W. E., Comisarow, M. B., Olah, G. A.: J. Am. Chem. Soc. 86, 4195 (1964).
Olah, G. A., Lukas, J.: J. Am. Chem. Soc. 90, 933 (1968).
Koch, H., Haaf, W.: Ann. 638, 111 (1960).
Schleyer, P. v. R., Watts, W. E., Fort, R. C., Jr., Comisarow, M. B., Olah, G. A.: J. Am. Chem. Soc. 86, 5679 (1964) and references cited therein. Saunders, M., Schleyer, P. v. R., Olah, G. A.: J. Am. Chem. Soc. 86, 5680 (1964).
Mateescu, G. D., Olah, G. A., private communication.
Fry, J. L., Harris, J. M., Bingham, R. C., Schleyer, P. v. R.: J. Am. Chem. Soc. 92, 2540 (1970).
Fort, R. C., Jr., Schleyer, P. v. R.: J. Am. Chem. Soc. 86, 4194 (1964).
Schleyer, P. v. R., Lam, L. K. M., Raber, D. J., Fry, J. L., McKervey, M. A., Alford, J. R., Cuddy, B. D., Keizer, V. G., Geluk, H. W., Schlatmann, J. L. M. A.: J. Am. Chem. Soc. 92, 5246 (1970).
Brouwer, D. M., Hogeveen, H.: Rec. Trav. Chim. 89, 211 (1970).
Olah, G. A.: private communication.
Saunders, M.: private communication.
Carpenter, C.: Ph. D. Thesis, Pennsylvania State University, 1967.
Raber, D. J., Bingham, R. C., Harris, J. M., Fry, J. L., Schleyer, P. v. R.: J. Am. Chem. Soc. 92, 5977 (1970).
McKervey, M. A., Alford, J. R., McGarrity, J. F., Rea, E. J. F.: Tetrahedron Letters 5165 (1968).
Geluk, H. W., Schlatmann, J. L. M. A.: Rec. Trav. Chim. 88, 13 (1969).
Vais, J., Burkhard, J., Landa, S.: Z. Chem. 9, 268 (1969).
Koch, H., Haaf, W.: Angew. Chem. 72, 628 (1960).
Geluk, H. W., Schlatmann, J. L. M. A.: Tetrahedron 24, 5361 (1968).
Sun Oil Co., Neth. Appl. 6, 511, 851; cf. Chem. Abstr. 65, 3768b (1966).
Geluk, H. W., Schlatmann, J. L. M. A.: Chem. Commun. 426 (1967).
Landa, S., Burkhard, J., Vais, J.: Z. Chem. 7, 388 (1967).
Burkhard, J., Vais, J., Landa, S.: Z. Chem. 9, 29 (1969).
Wishnok, J. S., Schleyer, P. v. R., Nickon, A., Pandit, G., Williams, R.: to be published. cf. Vogt, B. R., Suter, S. R., Hoover, J. R. E.: Tetrahedron Letters 1609 (1968).
Nickon, A., Pandit, G. D., Williams. R. O.: Tetrahedron Letters, 2851 (1967).
Sinnott, M. L., Storesund, H. J., Whiting, M. C.: Chem. Commun. 1000 (1969).
Curan, W. V., Angier, R. B.: J. Org. Chem. 34, 3668 (1969).
Cuddy, B. D., Grant, D., McKervey, M.A.: Chem. Commun. 27 (1971).
Stetter, H., Tacke, P.: Chem. Ber. 96, 694 (1963).
Alford, J. R., McKervey, M. A.: Chem. Commun. 615 (1970).
Black, R. M., Gill, G. B.: Chem. Commun. 972 (1970).
Lunn, W. H. W.: J. Chem. Soc. (C) 2124 (1970).
Vogt, B. R.: Tetrahedron Letters 1575 (1968).
Prelog, V., Seiwerth, R.: Chem. Ber. 74, 1644 (1951).
Baldwin, J. E., Fogelsong, W. D.: J. Am. Chem. Soc. 90, 4303 (1968).
Cupas, C. A., Schumann, W., Heyd, W. E.: J. Am. Chem. Soc. 92, 3237 (1970).
Spurlock, L. A., Clark, K.P.: J. Am. Chem. Soc. 92, 3829 (1970).
Belanger, A., Poupart, J., Deslongchamps, P.: Tetrahedron Letters 2127 (1968).
-, Lambert, Y., Deslongchamps, P.: Can. J. Chem. 47, 795 (1969).
Bingham, R. C., Schleyer, P. v. R., Lambert, V., Deslongchamps, P.: Can. J. Chem. 48, 3739 (1970).
Gauthier, J., Deslongchamps, P.: Can. J. Chem. 45, 297 (1967).
Whitlock, H. W., Jr: J. Am. Chem. Soc. 84, 3412 (1962).
Adachi, K., Naemura, K., Nakazaki, M.: Tetrahedron Letters 5467 (1968).
Tichy, M., Sicher, J.: Tetrahedron Letters 4609 (1969).
Jacobson, T.: Acta Chem. Scand. 21, 2235 (1967).
Baum, J. W., Gutsche, C. D.: J. Org. Chem. 33, 4312 (1968).
Breslow, D. S., Edwards, E. I., Leone, R., Schleyer, P. v. R.: J. Am. Chem. Soc. 90, 7097 (1968).
Bingham, R. C., Schleyer, P. v. R.: J. Am. Chem. Soc., in Press.
Nordlander, J. E., Jindal, S. P., Schleyer, P. v. R., Fort, R. C., Jr., Harper, J. J., Nicholas, R. D.: J. Am. Chem. Soc. 88, 4475 (1966).
Liggero, S. H., Sustmann, R., Schleyer, P. v. R.: J. Am. Chem. Soc. 91, 4571 (1969).
Imhoff, M. A., Summerville, R. H., Schleyer, P. v. R., Martinez, A. G., Hanack, M., Dueber, T. E., Stang, P. J.: J. Am. Chem. Soc. 92, 3802 (1970).
Bott, K.: Tetrahedron Letters 1747 (1969); Kell, D. R., McQuillin, F. J., Chem. Commun. 599 (1970); cf. Sasaki, T., Eguchi, S., Toru, T.: Chem. Commun. 780 (1968).
Bott, K.: Chem. Commun. 1349 (1969).
Nordlander, J. E., Wu, F. Y.-H., Jindal, S. P.: J. Am. Chem. Soc. 91, 3962 (1969).
Schlatmann, J. L. M. A., Korsloot, J. G., Schut, J.: Tetrahedron 26, 949 (1970). Also see Berezin, G. H.: Ger. offen. 1, 945, 208, March 19, 1970; Chem. Abstr. 73, 3544y (1970).
Schleyer, P. v. R., Funke, E., Liggero, S. H.: J. Am. Chem. Soc. 91, 3965 (1969).
Black, R. M., Gill, G. B.: J. Chem. Soc. (C) 671 (1970).
Gleicher, G. J., Schleyer, P. v. R.: J. Am. Chem. Soc. 89, 582 (1967).
Braun, P. B., Hornstra, J., Leenhouts, J. I.: unpublished results cited in Ref. 102).
Korsloot, J. G., Keizer, V. G., Schlatmann, J. L. M. A.: Rec. Trav. Chim. 88, 447 (1969).
Narayanan, V. L., Selescak, L.: J. Heterocycl. Chem. 6, 445 (1969).
Korsloot, J. G., Keizer, V. G.: Tetrahedron Letters 3517 (1969).
Sasaki, T., Eguchi, S., Toru, T.: J. Am. Chem. Soc. 91, 3390 (1969);-J. Org. Chem. 35, 4109 (1970).
---Chem. Commun. 1285 (1969).
Eakin, M., Martin, J., Parker, W.: Chem. Commun. 955 (1967).
Doyle, M. P., Parker, W.: Chem. Commun. 319 (1969).
Eakin, M. A., Martin, J., Parker, W.: Chem. Commun. 298 (1968).
Wiseman, J. R., Pletcher, W. A.: J. Am. Chem. Soc. 92, 956 (1970) and references cited therein.
Marshall, J. A., Faubl, H.: J. Am. Chem. Soc. 92, 948 (1970).
Wiseman, J. R., Chong, J. A.: J. Am. Chem. Soc. 91, 7775 (1969).
Marshall, J. A.: Accounts Chem. Res. 2, 33 (1969).
Gagosian, R. B., Dalton, J. C., Turro, N. J.: J. Am. Chem. Soc. 92, 4752 (1970).
Eakin, M., Martin, J., Parker, W.: Chem. Commun. 206 (1965).
Gagneux, A. R., Meier, R.: Tetrahedron Letters 1365 (1969).
Drew, M. G. B.: unpublished results.
Vegas, M. R., Wells, R. J.: Tetrahedron Letters 2565 (1969).
Sasaki, T., Eguchi, S., Kiriyama, T.: J. Am. Chem. Soc. 91, 212 (1969).
Mori, T., Yang, K. H., Kumoto, K., Noyaki, H.: Tetrahedron Letters 2419 (1970).
Vogt, B. R., Hoover, J. R. E.: Tetrahedron Letters 2841 (1967).
Webster, O. W., Sommer, L. H.: J. Org. Chem. 29, 3103 (1964).
Vogt, B. R., Suter, S. R., Hoover, J. R. E.: Tetrahedron Letters 1609 (1968).
Freeman, P. K., Rao, V. N. M., Bigam, G. E.: Chem. Commun. 511 (1965).
-Kinnel, R. B., Ziebarth, T. D.: Tetrahedron Letters 1059 (1970).
Sauers, R. R., Schinski, W., Mason, M. M.: Tetrahedron Letters 79 (1969); cf., Sauers, R. R., Sickles, B. R.: Tetrahedron Letters 1067 (1970).
Ref. 95) and references cited therein.
Udding, A. C., Strating, J., Wynberg, H., Schlatmann, J. L. M. A.: Chem. Commun. 657 (1966).
Pincock, R. E., Torupka, E. J.: J. Am. Chem. Soc. 91, 4593 (1969).
Baldwin, J. E., Foglesong, W. D.: J. Am. Chem. Soc. 90, 4303 (1968).
Yurchenko, A. G., Voroshchenko, A. T., Stepanov, F. N.: Zh Organ. Khim. 6, 189 (1970).
Liggero, S. H.: unpublished observations. cf. Stepanov, F. N., Guts, S. S.: Izv. Akad. Nauk SSSR, Ser. Khim. 439 (1970); Chem. Abstr. 73, 3518 (1970).
Sasaki, T., Eguchi, S., Toru, T., Ito, K.: Bull. Chem. Soc. Japan 43, 1820 (1970).
Mori, T., Kimoto, K., Kawanisi, M., Nozaki, H.: Tetrahedron Letters 3653 (1969).
Liggero, S. H., Majerski, Z., Schleyer, P. v. R.: Chem. Commun. 949 (1970).
Thielecke, W.: unpublished results.
Donohue, J., Goodman, S. H.: Acta Cryst. 22, 352 (1967); cf. Nordman, C. E., Schmitkons, D. L.: Acta Cryst. 18, 764 (1965).
Schleyer, P. v. R., Williams, J. E., Blanchard, K. R.: J. Am. Chem. Soc. 92, 2377 (1970).
Bratton, W. K., Szilard, I., Cupas, C. A.: J. Org. Chem. 32, 2019 (1967). Mansson, M., Rapport, N., Westrum, E. F., Jr.: J. Am. Chem. Soc. 92, 7296 (1970).
Lide, D. R., Jr.: J. Chem. Phys. 33, 1514 (1960).-Kuchitsu, K.: Bull. Chem. Soc. Japan 32, 748 (1959).-Bonham, R. A., Bartell, L. S.: J. Am. Chem. Soc. 81, 3419 (1959).-Bonham, R. A., Bartell, L. S., Kohl, D. A.: J. Am. Chem. Soc. 81, 4765 (1959).-Norman, N., Marhisen, H.: Acta Chem. Scand. 15, 1747 (1961)
Lide, D. R., Jr.: J. Chem. Phys. 33, 1519 (1960).
Atkinson, V. A.: Acta Chem. Scand. 15, 599 (1961).-Atkinson, V. A., Hassel, O.: Acta Chem. Scand. 13, 1737 (1959). Davis, M., Hassel, O.: Acta Chem. Scand. 17, 1181 (1963).
Williams, J. E., Stang, P. J., Schleyer, P. v. R.: Ann. Rev. Phys. Chem. 19, 531 (1968).
Allinger, N. L., Tribble, M. T., Miller, M. A., Wertz, D. H.: J. Am. Chem. Soc., to be published.
American Petroleum Institute Project 44; Selected Values of the Thermodynamic Properties of Hydrocarbons, Carnegie Institute of Technology, Pittsburgh, Pa., 1952 onwards.
Fort, R. C., Jr., Schleyer, P. v. R.: J. Org. Chem. 30, 789 (1965).
Liggero, S. H., Schleyer, P. v. R., Ramey, K. C.: Spectr. Letters 2, 197 (1969).
Taft, R. W.: Steric Effects in Organic Chemistry, p. 615; M. Newman, Ed. New York: Wiley 1956.
Smyth, C. P.: Dielectric Structure and Behavior. New York: McGraw-Hill 1955
Fort, R. C., Jr., Lundstrom, T. R.: Tetrahedron 23, 3227 (1967).
van Dursen, F. W., Korver, P. K.: Tetrahedron Letters 3923 (1967); cf. van Dursen, F. W., Udding, A. C.: Rec. Trav. Chim. 87, 1243 (1968).
Wahl, G. H., Jr., Peterson, M. R., Jr.: Chem. Commun. 1167 (1970).-Cockerill, A. F., Rackham, D. M.: Tetrahedron Letters 5149, 5153 (1970).
Olah, G. A., Lukas, J.: J. Am. Chem. Soc. 90, 933 (1968).
Bowers, K. W., Nolfi, G. J., Jr., Greene, F. D.: J. Am. Chem. Soc. 85, 3707 (1963).
Jones, M. T.: J. Am. Chem. Soc. 88, 174 (1966).
Gerson, F., Heilbroner, E., Heinzer, J.: Tetrahedron Letters 2095 (1966).
Bowers, K. W., Nolfi, G. J., Lowry, T. H., Greene, F. D.: Tetrahedron Letters 4063 (1966).
Jensen, F. R., Smart, B. E.: J. Am. Chem. Soc. 91, 5686 (1969).
Fujimoto, H., Kitagawa, Y., Hao, H., Fukui, K.: Bull. Chem. Soc. Jap. 43, 52 (1970).
Grob, C. A., Schwarz, W., Fischer, H. P.: Helv. Chim. Acta 47, 1385 (1964).
Sargent, G. D.: Quart. Rev. (London) 20, 301 (1966), and references cited therein.
Schleyer, P. v. R., Donaldson, M. M., Watts, W. E.: J. Am. Chem. Soc. 87, 375 (1965).
Schleyer, P. v. R., Stang, P. J., Raber, D. J.: J. Am. Chem. Soc. 92, 4725 (1970).
Olah, G. A., Calin, M.: J. Am. Chem. Soc. 90, 938 (1968).
Doleysek, Z., Hala, S., Hanus, S., Landa, S.: Collection Czech. Chem. Commun. 31, 435 (1966).
Mislow, K.: Introduction to Stereochemistry, p. 13–23. New York: Benjamin 1965.
Dallinga, G., Toneman, L. H.: Rec. Trav. Chim. 87, 795 (1968); cf. Chiang, J. F., Wilcox, C. F., Bauer, S. H.: J. Am. Chem. Soc., 90 3149 (1968).
Alden, R., Kraut, J., Traylor, T. G.: J. Am. Chem. Soc. 90, 74 (1968) and references cited therein.
Mislow, K.: Tetrahedron Letters 1415 (1964).
Tori, K., Hata, Y., Muneyuki, R., Takano, Y., Tsuji, T., Tanida, H.: Can. J. Chem. 42, 926 (1964).
Anderson, G. L., Stock, L. M.: J. Am. Chem. Soc. 91, 6804 (1969), cf. Maciel, G. E., Dorn, H. C.: J. Am. Chem. Soc., 93, 1268 (1971).
Wahl, G. H., Jr., Peterson, M. R., Jr.: J. Amer. Chem. Soc. 92, 7238 (1970).
Taft, R. W., Jr.: private communication.
Hamill, H., McKervey, M. A.: Chem. Commun. 864 (1969).
Applequist, J., Rivers, P., Applequist, D. E.: J. Am. Chem. Soc. 91, 5705 (1969).
Snatzke, G., Marquarding, D.: Ber. 100, 1710 (1967).
-, Eckhardt, G.: Ber. 101, 2010 (1968).
Briggs, S.W., Suchy, M., Djerassi, C.: Tetrahedron Letters 1097 (1968).
Snatzke, G., Ehrig, B. E., Klein, H.: Tetrahedron 25, 5601 (1969).See also Ref.367).
-, Eckhardt, G.: Tetrahedron 26, 1143 (1970).
--: Tetrahedron, 24, 4543 (1968).
Robinson, G. M., Wergang, O. E., Jr.: J. Am. Chem. Soc. 91, 3709 (1969).
Briggs, W. S., Suchy, M., Djerassi, C.: Tetrahedron Letters 1097 (1968).
Fort, R. C., Jr., Schleyer, P. v. R.: Advan. Alicycl. Chem. 1, 283 (1966).
Stetter, H., Schwarz, M., Hirschhorn, A.: Ber. 92, 1629 (1959).
Koch, H., Haaf, W.: Org. Syn. 44, 1 (1964) cf. Ref. 66).
Sasaki, T., Eguchi, S., Toru, T.: Bull. Chem. Soc. Japan, 41, 236 (1968).
Kovacic, P., Roskos, P. D.: J. Am. Chem. Soc. 91, 6457 (1969).
Bott, K.: Ber., 101, 564 (1968).
-, Hellmann, H.: Angew. Chem. 79, 932 (1967).
Kazanskii, B. A., Shokova, E. A., Korosteleva, T. V.: Izv. Akad. Nauk. SSSR, Ser. Khim. 2161 (1968); Chem. Abstr. 70, 77427x (1969).
Schneider, A.: U. S. Patent 3, 382, 288; Chem. Abstr. 69, 35584 (1968);-Warren, R. W.: Amer. Chem. Soc, Div. Petrol. Chem. Preprints, 15, B 56 (1970).
Kazanskii, B. A., Shokova, E. A., Korosteleva, T. V.: Dokl. Akad. Nauk. SSSR 188 (1969); Chem. Abst. 72, 3083b (1970).
Geluk, H. W., Schlatmann, J. L. M. A.: Tetrahedron 24, 5369 (1968).
Stetter, H., Weber, J., Wulff, C.: Ber. 97, 3488 (1964).
Stepanov, F. N., Dikolereko, E. J., Danilenko, G. J.: Zh. Org. Khim. 2, 640 (1966); Chem. Abstr. 65, 8732h (1966). cf. Ong. S. H., Chem. Commun. 1180 (1970).
Fort, R. C., Jr.: Ph. D. Thesis, Princeton University, 1964.
Osawa, E., Majerski, Z., Schleyer, P. v. R.: J. Org. Chem. 36, 205 (1971).
Fieser, L. F., Nazer, M. Z., Archer, S., Berberian, D. A., Slighter, R. G.: J. Med. Chem. 10, 517 (1967).
Landa, S., Burkhard, J., Vais, J.: Neftekhimiya 8, (1968); Chem. Abstr. 70, 3343v (1969).
Woodworth, C., Buss, V., Schleyer, P. v. R.: Chem. Commun. 569 (1968). See also Ref. 203).
Vais, J., Burkhard, J., Landa, S.: Z. Chem. 8, 303 (1968).
Raber, D. J., Fort, R. C., Jr., Wiskott, E., Woodworth, C. W., Schleyer, P. v. R., Weber, J., Stetter, H.: Tetrahedron in press.
Tabushi, I., Hamuro, J., Oda, R.: J. Org. Chem. 33, 2108 (1968).
Allinger, N. L., Miller, M. A., van Catledge, F. A., Hirsch, J. A.: J. Am. Chem. Soc. 89, 4345 (1967).
Fry, J. L.: unpublished results. cf. Fry, J. L., Schleyer, P. v. R.: Abstracts, 157th National Meeting of the American Chemical Society, Minneapolis, Minn., April, 1969, No. ORGN 133.
Haas, W. L., Krumkalns, E. V., Gerzon, K.: J. Am. Chem. Soc. 88, 1988 (1966). See also Jaeger, G. and Geiger, R.: Ber. 103, 1727 (1970).
Hoek, W., Wynberg, H., Strating, J.: Rec. Trav. Chim. 85, 1039 (1966).
-, Strating, J., Wynberg, H.: Rec. Trav. Chim. 85, 1045 (1966).
-, Wynberg, H., Strating, J.: Rec. Trav. Chim. 85, 1045 (1966).
Daeniker, H. U.: Helv. Chim. Acta. 50, 2008 (1967).
Windoly, T. B., Johnston, D. B. R.: Tetrahedron Letters 2555 (1967).
Boldt, P., Theilecke, W.: Angew. Chem. 78, 1058 (1966).
Rundel, W.: Ber. 99, 2707 (1966).
McKervey, M. A.: Chem. Ind. 1791 (1967).
Stepanov, F. N., Myrsima, R. A.: Zh. Organ. Khim. 2, 644 (1966); cf. Chem. Abstr., 65, 8783 (1966).
-, Danilenko, G. I.: Zh. Organ. Khim. 2 101 (1966); cf. Chem. Abstr. 65, 628a (1966).
-, Myrsima, R. A.: Zh. Organ. Khim. 3, 530 (1967); cf. Chem. Abstr., 67, 21484 (1967).
-, Damilenko, G. I.: Zh. Organ. Khim. 3, 533 (1967); cf. Chem. Abstr. 67, 21485 k (1967).
-, Stolyarov, Z. E.: Zh. Organ. Khim. 5, 91 (1969); Chem. Abstr., 70, 87122 (1969);-Caplidi, E. C., Leum, N. L.: U S. Patent 3, 433, 844; Chem. Abstr. 71, 3053 (1969);-Shuld, G., Moore, R. E.: U. S. Patent, 3, 255, 268; Chem. Abstr. 65, 8782 (1966).
Geigy, J. R., Geigy, A.-G.: Belg. Patent 629, 371; Chem. Abstr. 60, 9284 (1964).
Geigy, J. R., Geigy, A.-G.: Fr. Patent 1, 393, 617; Chem. Abstr. 63, 9838 f (1965).
Talaty, E. R., Dupuy, A. E., Jr., Cancienne, A. E., Jr.: J.Heterocyclic Chem. 4, 657 (1967).-Lengyel, I., Uliss, D. B.: Chem. Commun. 1621 (1968).-Bott, K.: Tetrahedron Letters 3323 (1968).-Talaty, E. R., Dupuy, A. E., Jr.: J. Med. Chem. 12, 195 (1969).-Talaty, E. R., Dupuy, A. E., Jr., Golson, T. N.: Chem. Commun. 49 (1969).-cf. Lengyel, I., Uliss, D. B., Mark, R. U.: J. Org. Chem. 35, 4077 (1970).
Bott, K.: Angew. Chem. 7, 894 (1968).
Stepanov, F. N., Dovgan, D. L.: Zh. Organ. Khim. 4, 277 (1968); Chem. Abstr. 68, 104612 (1968).
Squibb, E. R.: Neth. Appl. 6, 613, 232; Chem. Abstr. 68, 68538 (1968).
Stetter, H., Last, W.: Ber. 102, 3364 (1969).
Sasaki, T., Eguchi, S., Toru, T.: Bull. Chem. Soc. Japan 42, 3613 (1969).
Chakrabarti, J. K., Foulis, M. J., Szinai, S. S.: Tetrahedron Letters 6249 (1968).
Sasaki, T., Eguchi, S., Toru, T.: Bull. Chem. Soc. Japan 41, 238 (1968).
Stepanov, F. N., Isaev, S. D., Vasil'eva, Z. P.: Zh. Organ. Khim. 6, 51 (1970); Chem. Abstr. 72, 89874 (1970).
Stetter, H., Krause, M., Last, W.: Ber. 102, 3357 (1969).
Bernstein, J.: U. S. Patent 3, 379, 754; Chem. Abstr. 69, 51731 (1968).
Stepanov, F. N., Dovgan, N. L.: Zh. Organ. Khim. 6, 55 (1970); Chem. Abstr. 72, 89866 (1970).
Stetter, H., Gartner, J., Tacke, P.: Angew. Chem. 77, 171 (1965); Ber. 98, 388 (1965).
--Angew. Chem. 925 (1966).
Landa, S., Vais, J., Burkhard, J.: Z. Chem. 7, 233 (1967).
Stepanov, F. N., Baklan, V. F.: Zh. Organ. Khim. 1, 579 (1965); cf. J. Org. Chem. USSR 1, 580 (1965).
--, Isaev, S. D.: Zh. Organ. Khim. 1, 280 (1965); cf. J. Organ. Chem. USSR 1, 270 (1965).
-, Damilenko, G. I.: Zh. Organ. Khim. 3, 914 (1967); cf. Chem. Abstr. 67, 63950 (1967).
-Srebrodol'skij, Y. I.: Sintez Prirodn. Soedin., ikh Analogov i Fragmentov, Akad. Nauk SSSR, Otd. Obshch, i Tekhn Khim. 97 (1965); cf. Chem. Abstr. 65, 627d. (1966).
Grob, C. A., Schwarz, W.: Helv. Chim. Acta 47, 1870 (1964).
Schneider, A.: Ger. Patent 1, 913, 998; Chem. Abstr. 72, 21405 (1970).
Talaty, E. R., Cancienne, A. E., Jr, Dupuy, A. E., Jr.: J. Chem. Soc., (C), 1902 (1968).
Danilenko, G. I., Krayushkin, M. M., Sevost' yanova: U. U., Izv. Akad. Nauk SSSR, Ser. Khim. 444 (1970); cf. Chem. Abstr. 73, 3522 (1970).
Stepanov, F. N., Baklan, V. F.: Zh. Organ. Khim. 2, 1635 (1966); J. Org. Chem. USSR 2, 1611 (1966).
-, Srebrodol'skii, Y. I.: Zh. Organ. Khim. 2, 1612 (1966); Chem. Abstr. 66, 64766 (1967).
Gerzon, K., Tobias, D. J., Holmes, R. E., Rathbun, R. E., Kattau, R. W.: J. Med. Chem. 10, 603 (1967).
Stetter, H., Krause, M.: Tetrahedron Letters 1841 (1967).
Sun Oil Co., Neth. Pat. Appl., 6, 605, 406; Chem. Abstr. 66, 115365 a (1967).
Muller, E., Trense, U.: Tetrahedron Letters 4979 (1967).
Moore, R. E.: Private communication.
Sun Oil Co., Brit. Patent 1, 108, 336; Chem. Abstr. 69, 35585 (1968).
Udding, A. C., Strating, J., Wynberg, H.: Tetrahedron Letters 1345 (1968).
Landa, S., Burkhard, J., Vais, J.: Z. Chem. 7, 388 (1967).
Landa, S., Vais, J., Burkhard, J.: Collection Czech. Chem. Commun. 32, 570 (1967).
Talaty, E. R., Dupuy, A. E., Jr.: Chem. Commun. 790 (1968).
Greidanus, J. W., Schwalim, W. J.: Can. J. Chem. 47, 3715 (1969); 48, 3530, 3593 (1970).
Scharp, J., Wynberg, H., Strating, J.: Rec. Trav. Chim. 89, 18 (1970).
Wynberg, H., Reiffers, S., Strating, J.: Rec. Trav. Chim. 89, 982 (1970).
Strating, J., Scharp, J., Wynberg, H.: Rec. Trav. Chim. 89, 23 (1970).
-Alberts, A. H., Wynberg, H.: Chem. Commun. 818 (1970).
-Wierings, J. H., Wynberg, H.: Chem. Commun. 907 (1969).
McKervey, M. A., Grant, D., Hamill, H.: Tetrahedron Letters 1975 (1970).
Gund, T. M., Nomura, M., Williams, V. Z. Jr., Schleyer, P. v. R., Hoogzand, C.: Tetrahedron Letters 4875 (1970).
Gund, T. M.: unpublished results.
Lenoir, D., Schleyer, P. v. R., Cupas, C. A., Heyd, W. E.: Chem. Commun. 26 (1971).
Smith, G. W., Williams, D.: J. Org. Chem. 26, 2207 (1961).
Tabushi, I., Hamuro, J., Oda, R.: J. Am. Chem. Soc. 89, 7127 (1969).
Owens, P. H., Gleicher, G. J., Smith, L. M., Jr.: J. Am. Chem. Soc. 90, 4122 (1968).
Gleicher, G. J., Jackson, J. L., Owens, P. H., Unruh, J. D.: Tetrahedron Letters 833 (1969).
Tabushi, I., Okada, T., Aoyama, Y., Oda, R.: Tetrahedron Letters 4069 (1969).
Muller, E., Fiedler, G.: Ber. 98, 3493 (1965).
-Trense, U.: Tetrahedron Letters 2045 (1967).
Tabushi, I.: private communication.
Wiberg, K. B.: In: Oxidation in Organic Chemistry, p. 109–124, Wiberg, K. B., ed. New York: Academic Press 1965.
Bingham, R. C., Schleyer, P. v. R.: J. Org. Chem. in press. cf. Schleyer, P. v. R., Nicholas, R. D.: Abstracts, 140th National Meeting of the Amer. Chem. Soc., Chicago, III., September 1961, p. 75Q.
McKervey, M. A., Faulkner, D., Hamill, H.: Tetrahedron Letters 1971 (1970).
Curran, W. V., Angier, R. B.: Chem. Commun. 563 (1967).
Schleyer, P. v. R., Buss, V.: J. Am. Chem. Soc. 91, 5880 (1969).
Ree, B. R., Martin, J. C.: J. Am. Chem. Soc. 92, 1660 (1970); cf. Martin, J. C., Ree, B. R.: J. Am. Chem. Soc., 91, 5882 (1969).
Chakrabarti, J. K., Szinai, S. S., Todd, A.: J. Chem. Soc. (C) 1303 (1970).
Lunn, W. H. W., Podmore, W. D., Szinai, S. S.: J. Chem. Soc. 1657 (1968).
Stetter, H., Thomas, H. G., Meyer, K.: Ber. 103, 863 (1970).
Udding, A. C., Wynberg, H., Stating, J.: Tetrahedron Letters 5719 (1968).
Lee, C. M., Clardy, J. C.: Chem. Commun. 716 (1970).
Raber, D. J., Kane, G. J., Schleyer, P. v. R.: Tetrahedron Letters, 4117 (1970).
Janku, J., Landa, S.: Collection Czech. Chem. Commun. 35, 375, 3481 (1970).
Schlatmann, J. L. M. A.: private communication. See also Ref. 278).
Barton, D. H. R.: Science 169, 539 (1970).
Fort, R. C.: In: Carbonium Ions, Vol. III; Olah, G. A., Schleyer, P. v. R., eds. New York: Interscience, to be published.
Williams, J. E., Buss, V., Allen, L. C., Schleyer, P. v. R., Latham, W. A., Hehre, W. J., Pople, J. A.: J. Am. Chem. Soc. 92, 2141 (1970) and earlier papers in this series.-Buss, V., Schleyer, P. v. R., Allen, L. C.: J. Am. Chem. Soc., submitted for publication.
Bingham, R. C., Sliwinski, W. F., Schleyer, P. v. R.: J. Am. Chem. Soc. 92, 3471 (1970).-Sherrod, S. A., Bergmann, R. G., Gleicher, G. J., Morris, D.: J. Am. Chem. Soc. 92, 3469 (1970).
Fainberg, A. H., Winstein, S.: J. Am. Chem. Soc. 78, 2770 (1956) and references cited therein.
Kevill, D. N., Kolwyck, K. C., Weitl, F. L.: J. Am. Chem. Soc., 92, 7300 (1970).
Fry, J. L., Lancelot, C. J., Lam, L. K. M., Harris, J. M., Bingham, R. C., Raber, D. J., Hall, R. E., Schleyer, P. v. R.: J. Am. Chem. Soc. 92, 2538 (1970).
Schleyer, P. v. R., Fry, J. L., Lam, L. K. M., Lancelot, C. J.: J. Am. Chem. Soc. 92, 2542 (1970).-cf. Liggero, S. H., Harper, J. J., Schleyer, P. v. R., Krapcho, A. P., Horn, D. E., J. Am. Chem. Soc. 92, 3789 (1970).
Schleyer, P. v. R., Woodworth, C. W.: J. Am. Chem. Soc. 90, 6528 (1968).
Woodworth, C. W.: Ph. D. Thesis, Princeton University, 1969. For the rate constants of other substituted adamantanes in a different solvent see Krayushkin, M. M., Sevot'yanova, V. V., Danilenko, G. I.: Izv. Akad. Nauk SSSR, Ser. Khim. 2844 (1969); Chem. Abstr. 72, 78153 (1970).
Robinson, M. J. T.: private communivation, 1968.
Laurie, V. W., Muenter, J. S.: J. Am. Chem. Soc. 88, 2883 (1966).
Weber, J.: Dissertation, Technischen Hochschule, Aachen, 1966.
Grob, C. A., Schwarz, W.: Helv. Chim. Acta 47, 1870 (1964).
Taft, R. W., Jr.: Lewis, I. C.: J. Am. Chem. Soc. 80, 2436 (1958).
Tsuji, T., Moritani, I., Nishida, S., Tadokoro, G.: Tetrahedron Letters 1207 (1967); Bull. Chem. Soc. Japan 40, 2344 (1967).-Tsuji, T., Moritani, I., Nishida, S.: Bull. Chem. Soc. Japan, 40, 2338 (1967).
Hanstein, W., Berwin, H. J., Traylor, T. G.: J. Am. Chem. Soc. 92, 829 (1970).
Jensen, F. R., Smart, B. E.: J. Am. Chem. Soc. 91, 5686, 5688 (1969).
Dauben, W. G., Chitwood, J. L., Scherer, K. V.: J. Am. Chem. Soc., 90, 1014 (1968); cf. Dauben, W. G., Chitwood, J. L.: J. Am. Chem. Soc. 92, 1624 (1970).
Wiberg, K. B., Taylor, G. N., Klein, G. W., Williams, V. Z., Jr.: J. Am. Chem. Soc., submitted for publication.
For a recent, pertinent review see Rüchardt, C.: Angew. Chem. 82, 845 (1970), Internat ed. 9, 830(1970).
Applequist, D. E., Kaplan, L.: J. Am. Chem. Soc. 87, 2194 (1965).
Fort, R. C., Jr., Franklin, R. E.: J. Am. Chem. Soc. 90, 5267 (1968).-Lorand, J. P., Chodroff, S. D., Wallace, R. W.: J. Am. Chem. Soc, 90, 5266 (1968).-Humphrey, L. B., Hodgson, B., Pincock, R. E.: Can. J. Chem. 46,3099 (1968).
Oberlinner, A., Rüchardt, C.: Tetrahedron Letters 4685 (1969).
For a recent theoretical comparison of carbonium ions and free radicals by ab initio methods, sec Buss, V., Schleyer, P. v. R., Allen, L. C.: J. Am. Chem. Soc., in press.
Chick, W. H., Ong, S. H.: Chem. Commun. 216 (1969).
Prochazka, M., Ryba, O., Lim, D.: Collection Czech. Chem. Commun. 33, 3387 (1968).
See Ref. 311). and references cited therein. cf., however, Razuvaev, G. A., Bogulaskaya, L. S., Etlis, V. S., Brovkina, G. V.: Tetrahedron 25, 4925 (1969).
Tabushi, I., Hamuro, J., Oda, R.: J. Chem. Soc. Japan, 89, 789 (1968); Chem. Abstr., 70, 19645 (1969).
Lansbury, P. T., Sidler, J. D.: Chem. Commun. 373 (1965).
Rayner, D. R., Gordon, A. J., Mislow, K.: J. Am. Chem. Soc. 90, 4854 (1968).
Lansbury, P. T., Pattison, V. A., Sidler, J. D.: J. Am. Chem. Soc. 88, 78 (1966); cf. Lansbury, P. T., Sidler, J. D.: Tetrahedron Letters 691 (1965).
Davies, W. L., Grunert, R. R., Hoff, R. F., McGahen, J. W., Neumayer, E. M., Paulshock, M., Watts, J. C., Wood, T. R., Hermann, E. C., Hoffmann, C. E.: Science 144, 862 (1964).
Prusoff, W. H.: Pharmacol. Rev. 19, 234 (1967).
Herrmann, E. C., Jr.: In: Annual Reports in Medicinal Chemistry; Cain, C. K., ed. New York: Academic Press 1967, 1968.
Herrmann, E. C., Jr., Stinebring, W. R., eds.: Annals of the New York Academy of Sciences, Vol. 173, Part. I, 1970.
Wendel, H.: Federation Proc. 23, 387 (1964).
Jackson, G. G., Muldoon, R. L., Akers, L. W.: Antimicrobial Agents Chemotherapy 703 (1963).
Wendel, H.: Federation of Am. Soc. for Exptl. Biology, Abstracts 48th Annual Meeting, Chicago, Ill. April, 1964, #1719
Grunert, R. R., McGahen, J. W., Davies, W. L.: Virology 26, 262 (1965).
Neumayer, E. M., Hoff, R. F., Hoffmann, C. E.: Proc. Soc. Exptl. Biol. Med. 119, 393 (1965).
Davies, W. L., Grunert, R. R., Hoffmann, C. E.: J. Immunol. 95, 1090 (1965).
Bryans, J. T., Zent, W. W., Grunert, R. R., Boughton, D. C.: Nature 212, 1542 (1966).
Oxford, J. S., Shild, G. S.: Arch. Ges. Virusforsch. 17, 313 (1965); cf. Chem. Abstr. 64, 5469 (1965).
Cochran, K. W., Maassab, H. F., Tsunoda, A., Berlin, B. S.: Ann. N. Y. Acad. Sci. 130, 432 (1965).
Maassab, H. F., Cochran, K. W.: Science 145, 1443 (1964).
Oxford, J. S., Schild, G. C.: Brit. J. Exptl. Pathol. 48, 235 (1967).
Wallbank, A. M., Matter, R. E., Klinikowski, N. G.: Science 152, 1760 (1966).
Oker-Blom, N., Andersen, L.: European J. Cancer 2, 9 (1966); cf. Chem. Abstr. 65 1234 (1966).
Nornick, R. B., Togo, Y., Dawkins, A. T.: Am. Soc. Microbiol, Bacteriol. Proc. 313 (1966).
Wendel, H. A., Synder, M. T., Pell, S.: Chim. Parmacol. Therap. 7, 38 (1966).
Quilligan, J. J., Jr., Hirayama, M., Baemstein, H. D., Jr.: J. Pediat. 69, 572 (1966).
Lee, S. H. S., Dobson, R. P., van Rooyen, C. E.: Chemotheropia 11, 163 (1966).
Hoffmann, C. E., Neumann, E. M., Hoff, R. F., Goldsberg, R. A.: J. Bacteriol. 90, 623 (1965).
Hornick, R. B., Togo, Y., Mahler, S., Iezzoni, D.: Ann. N. Y. Acad. Sci. 173, 10 (1970); Herrmann, E. C., Jr., Stinebring, W. R., eds.-cf. McGahen, J. W. Neumayer, E. M., Grunnert, R. R., Hoffmann, C. E.: Ann. N. Y. Acad. Sci., 173, 557 (1970); Herrmann, E. C., Jr., Stinebring, W. R., eds.
For an additional recent survey of this area see Gerzon, K., Krumkalns, E. V., Kau, D.: Symposium Abstracts, 159th Meeting of the Am. Chem. Soc., Division of Petroleum Chemistry, Houston, Texas, Feb. 1970, p. B80.
Gerzon, K., Krumkalns, E. V., Brindle, R. L., Marshall, F. J., Root, M. A.: J. Med. Chem. 6, 760 (1963).
Rapalo, R. T., Kroay, R. J., Gerzon, K.: J. Med. Chem. 8, 850 (1965).
Gerzon, K., Kau, D.: J. Med. Chem. 10, 189 (1967).
Bleidner, W. E., Harmon, J. B., Hewes, W. E., Lynes, T. E., Hermann, E. C.: J. Pharmacol. Exptl. Therap. 150, 484 (1965).
Wood, T. R.: Ann. N. Y. Acad. Sci. 130, 1, 419 (1965).
Korytnyk, W., Fricke, G.: J. Med. Chem. 11, 180 (1968).
Jacobs, T. L., Muscio, O. J., Jr.: Tetrahedron Letters 4829 (1970).
Kreuzberger, A. and Schroders, H.-H.: Tetrahedron Letters 4523 (1970).
--Tetrahedron Letters 4921 (1970).
Bagrii, E. I., Frid, T. Yu, Sanin, P. I.: Izv. Nauk SSSR, Ser. Khim., 498 (1970); Chem. Abstr. 73, 3513 (1970).
Yurchenko, A. G., Stepanov, F. N., Isaeva, S. S., Zolotarev, B. M., Kadentsev, V. I., and Chizhov, O. S.: Org. Mass. Spectrom. 3, 1401 (1970).
Warren, R. W., Schneider, A. and Moore, R. E.: Appl. Spectrosc. 22, 58 (1968).
Chadwick, D., Legon, A. C.and Millen, D. J.: J.Chem. Soc. (A), 1117 (1968).
Pistorius, C. W. and Resing, H. A.: Mol. Cryst. 5, 353 (1969).
Wood, D. E. and Lloyd, R. V.: J. Chem. Phys., 52, 3840 (1970).-J. Chem. Phys., 53, 3932 (1970).-and Pratt, D. W.; J. Amer. Chem. Soc., 92, 4115 (1970).
Gee, D. R., Fabes, L. and Wan, J. K. S.: Chem. Phys. Lett., 7, 311 (1970).
Yoshida, Z., Tabushi, I. and Takahashi, N.: J. Amer. Chem. Soc., 92, 6670 (1970).
Kovacic, P. and Chang, J.-H.C.: Chem. Commun. 1460 (1970).
Stepanov, F. N., Sukhoverklov, V. D., Baklan, V. F. and Yurchenko, A. G.: Zh. Org. Khim. 6, 884 (1970); Chem. Abstr. 73, 14282 (1970).
Wieringa, J. H., Strating, J. and Wynberg, H.: Tetrahedron Letters 4579 (1970).
Wynberg, H., Boelema, E., Wieringa, J. H. and Strating, J.: Tetrahedron Letters, 3613 (1970).
van Zorge, J. A., Strating, J. and Wynberg, H.: Rec. Trav. Chim. 89, 781 (1970).-cf. Stepanov, F. N. and Guts, S. S.: Zh. Organ. Khim., 4, 1933 (1968); Chem. Abstr. 70, 28456 (1969).
Geneste, P., Lamaty, G., Moreau, C. and Roque, J-P.: Tetrahedron Letters 5011 (1970).
Dalton, J. C., Pond, D. M. and Turro, N. J.: J. Amer. Chem. Soc., 92, 2173 (1970).
Herr, M. E., Johnson, R. A., Krueger, W. C., Murray, H. C. and Pschigoda, L. M.: J. Org. Chem. 35, 3607 (1970) and references cited therein.
Ning, N. Y. and Sternbach, L. H.: J. Med. Chem. 6, 1251 (1970).
Kevill, D. N. and Wertl, F. L.: J. Org. Chem. 35, 2526 (1970).
Krusic, P. J., Rettig, T. A., and Schleyer, P. v. R.: J. Amer. Chem. Soc., submitted for publication.
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Bingham, R.C., Schleyer, P.v.R. (1971). Recent developments in the chemistry of adamantane and related polycyclic hydrocarbons. In: Chemistry of Adamantanes. Fortschritte der Chemischen Forschung, vol 18/1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0051406
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