Abstract
The process of waste minimisation has many facets. One major goal must be to enhance the intrinsic selectivity of any given process so that less waste is produced. A second is to provide a means of recovering reagents in a form which allows easy collection and regeneration. Yet another is to replace stoichiometric processes by catalytic ones. Solids, as catalysts or as supports for other reagents, offer potential for benefit in all of these areas.
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References
G. Bram, E. d’Incon and A. Loupy, New J. Chem. 1982, 6, 689.
A. Cornelis and P. Laszlo, Synthesis 1985, 909.
P. Laszlo, Chem. Ind. 1994, 53, 429.
Solid Supports and Catalysts in Organic Synthesis (ed K. Smith), Ellis Horwood Ltd., Chichester, 1992.
F. Pautet and M. Daudon, Tetrahedron Lett. 1991, 32, 1457.
K. Smith, M. Butters and B. Nay, Tetrahedron Lett. 1988, 29, 1319.
K. Smith, M. Butters and W.E. Paget, Synthesis 1985, 1155.
M. Kodomari, S. Takahashi and S. Yoshitomi, Chem. Lett. 1987, 1901.
M. Hojo and R. Masuda, Tetrahedron Lett. 1976, 613.
L. Delaude and P. Laszlo, J. Org. Chem. 1990, 55, 5260.
K. Smith, M. Butters and B. Nay, Synthesis 1985, 1157.
Y. Higuchi and T. Suzuki, J. Synth. Meth. 1984, 10, 77881Z.
A.G. Mistry, K. Smith and M.R. Bye, Tetrahedron Lett. 1986, 27, 1051.
H. Konishi, K. Aritomi, T. Okano and J. Kiji, Bull. Chem. Soc. Jpn. 1989, 62, 591.
A.P. Lecuyer, J.L. Luche, H.B. Kagan, G. Collin and C. Mazieres, Bull. Soc. Chim. Fr. 1973, 1690.
F. de la Vaga and Y. Sasson, J. Chem. Soc, Chem. Commun. 1989, 653.
M. Onaka and Y. Izumi, Chem. Lett. 1984, 2007.
K. Smith, K. Fry, M. Butters and B. Nay, Tetrahedron Lett. 1989, 30, 5333.
S.M. Nagy, K.A. Yarovoy, M.M. Shakirov, V.G. Shubin, L.A. Vostrikova and K.G. Ione, J. Mol. Catal. 1991, 64, L31.
A. Cornelis, A. Gerstmans and P. Laszlo, Chem. Lett. 1988, 1839.
A. Cornelis, P. Laszlo and P. Pennelneau, Bull. Soc. Chim. Belg. 1984, 93, 961.
J.M. Bakke, J. Liaskan and G.B. Loretzen, J. Prakt. Chem. 1982, 324, 488.
P. Laszlo and J. Vandormael, Chem. Lett. 1988, 1843.
S. Daley, K.A. Trevor, K.R. Randles and B.D. Gott, PCT Int. Patent Appl. W093/ 18 000.
USP 2 930 820/1960.
USP 2 945 072/1960.
A. Corma, H. Garcia and J. Primo, J. Chem Res (S) 1988, 40.
EP 160144/1985.
S. Sivasanker and A. Thangaraj, J. Catal. 1992, 138, 386.
J. Haggin, Chem. Eng. News. 1990, 6th August, 29.
Y. Kamitori, M. Hojo, R. Masuda, T. Izumi and S. Tsukamoto, J. Org. Chem. 1984, 49, 4146.
S.H. Baek, M. Srebnik and R. Mechoulam, Tetrahedron Lett. 1988, 29, 1319.
R.K. Razdan, H.C. Dazell and G.R. Handrick, J. Am. Chem. Soc. 1974, 96, 5860.
USP 4 052 466/1977.
A.H. Jackson, R. Pandey, K.R.N. Rao and E. Roberto, Tetrahedron Lett. 1985, 26, 793.
A.P. Singh, Catal. Lett. 1992, 16, 43.
Z. Iqbal, A.H. Jackson and K.R.N. Rao, Tetrahedron Lett. 1988, 29, 2577.
B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Graille and D. Poch, J. Mol. Catal. 1987, 47, 229.
FR 2 599 275/1987.
JP 60, 52 436/1985.
B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Graille and D. Ploch, J. Org. Chem. 1986, 51, 2128.
B. Coq, V. Gourves and F. Figueras, Appl. Catal A 1993, 100, 69.
K.G. Ione, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim, Nauk 1990, 103.
M. S. Rigutto, H.J.A. deVries, S.R. Magil, A.J. Hoefnagel and H. van Bekkum, Stu. Surf. Sci. Catal. 1993, 78, 661.
P. Bhattachryya and S.S. Jash, Indian J. Chem., Sect. B 1987, 26, 1177.
J. Cabral, P. Laszlo and M.T. Montaufier, Tetrahedron Lett. 1988, 29, 547.
J. Yamawaki, T. Ando and T. Hanafusa, Chem. Lett. 1981, 1143.
K. Sukala, Bull. Chem. Soc. Jpn. 1985, 58, 383.
M. Onaka, A. Umezono, M. Kawai and Y. Izumi, J. Chem. Soc., Chem. Commun. 1985, 1202.
R.K. Sabu, R. Sukumar and M. Lalithamika, Bull. Chem. Soc. Jpn. 1993, 66, 3535.
USP 4 053 286/1977; E. Paul, Chem. Ind. (London) 1990, 10, 320.
B. Renger, Synthesis 1985, 856.
H. Ogawa, Y. Ichimura, T. Chihara, S. Teratani and K. Taya, Bull. Chem. Soc. Jpn. 1986, 59, 2481.
G. Henning, Prog. Inorg. Chem. 1959, 1, 125.
J. Bertin, H.B. Kagan, J.L. Luche and R. Setton, J. Am. Chem. Soc. 1974, 96, 8113.
G. Posner and M. Oda, Tetrahedron Lett. 1981, 22, 5003.
D.P. Roelofsen, J.W.M. DeGraaf, J.A. Hagendoorn, M.H. Verschoor and H. van Bekkum, Recl. Trav. Chim. Pays-Bas. 1970, 89, 193.
P. Gros, P. LePerchec, P. Cauthier and J.P. Senet, Synth. Commun. 1993, 23, 1835.
J.A. Ballantine, J.H. Purnell and J.M. Thomas, Clay Miner. 1983, 18, 347.
J.H. Purnell and J.A. Ballantine, J. Mol. Catal. 1984, 27, 169.
C. Gagnien and A. Grouillier, Carbohydr. Res. 1980, 84, 61.
J.C. Florent and C. Monneret, J. Chem. Soc, Chem. Commun. 1987, 1171.
D.P. Roelofsen, E.R.J. Wils and H. van Bekkum, Recl. Trav. Chim. Pays-Bas 1971, 90, 1141.
D.P. Roelofsen and H. van Bekkum, Synthesis 1972, 419.
T.M. Wartel, W.H. Esser, G. van Minnen-Pathuis, R. Taol, D.P. Roelofsen and H. van Bekkum, Recl. Trav. Chim. Pays-Bas 1977, 96, 44.
M.V. Joshi and CS. Narasimhan, J. Catal. 1993, 141, 308.
H. Paulsen and R. Lebuhn, Liebigs Ann. Chem. 1983, 1047.
P. Garegg, C. Hendrichson, J. Noeberg and P. Ossowsk, Carbohydr. Res. 1983, 119, 95.
P. Lescure and F. Huet, Synthesis 1987, 404.
G.H. Posner and D.Z. Rogers, J. Am. Chem. Soc. 1977, 99, 8208.
G.H. Posner and D.Z. Rogers, J. Am. Chem. Soc. 1977, 99, 8214.
J. Riego, A. Costa and J.M. Sao, Chem. Lett. 1986, 1565.
USP 4 620 044/1986; CA: 106, 84049r.
M. Onaka, M. Kawai and Y. Izumi, Chem. Lett. 1985, 779.
M. Onaka, K. Sugita and Y. Izumi, J. Org. Chem. 1989, 54, 1116.
M. Ochpai, T. Ukita and E. Fujika, Chem. Lett. 1983, 1457.
D. Lebar, L. Heresi, W. Dumont and A. Krief, Tetrahedron Lett. 1978, 1141.
D. Lebar, L. Heresi, W. Dumont and A. Krief, Tetrahedron Lett. 1978, 1145.
J.H. Markgraf, E.W. Greeno, M.D. Miller and W.J. Zaks, Tetrahedron Lett. 1983, 24, 241.
J. Yamawaki, T. Kawate, T. Ando and T. Hanafusa, Bull. Chem. Soc. Jpn. 1983, 56, 1885.
A. Vigerani, M. Foglio, G. Franceschi, P. Masi, A. Suarato, E. Gandini and G. Palamidessi, J. Chem. Soc, Perkin Trans. 1 1979, 504.
FR 2 670 209/1993. CA: 1993, 118, 38763u.
M. Brand and S.E. Drewes, Synth. Commun., 1987, 17, 795.
R. Sreekumar, Y.V.S. Navayana Murthy and C. Narayana Pillai, J. Chem. Soc, Chem. Commun. 1992, 22, 1624.
H. Ogawa, K. Nozawa and P. Ahn, J. Chem. Soc, Chem. Commun. 1993, 18, 1393.
N.E. Martil and F.A. de la Cruz, An. Ouim. 1985, Sev B, 81, 22.
D. Fishman, J.T. Klug and A. Shani, Synthesis 1981, 137.
L.R.M. Markens, W. Vermeinen, P. Grobet and P. Jacobs, Preparation of Catalysts IV 1987, 531.
USP 4 503 282/1985; CA: 103, 6846x.
EP 100117/1983.
Q. Wang and Z. Chen, Kexue Tongboa 1984, 29, 1130.
M.D. Bachi and J. Vaya, Tetrahedron Lett. 1977, 2209.
T. Matsuda and E. Kikuchi, Proc. Int. Conf. Pet. Refin. Petrochem. Process 1991, 2, 714
T. Matsuda and E. Kikuchi, CA, 188, 126889 r.
J.A. Marshall, N.H. Andersen and P.C. Johnson, J. Org. Chem. 1970, 35, 186.
M.G. Ryzkov, J. Synth. Meth. 1983, 9, 75500Y.
D. Brunei and M. Chamoumi, J. Mol. Catal. 1993, 79, 297.
A.J. Hoefnage and H. van Bekkum, Appl. Catal. A 1993, 97, 87.
G.V.M. Sharma, B.M. Choudary, R.M. Sharma and K.K. Rao, J. Org. Chem. 1989, 54, 2997.
I. Yamaguchi, Y. Joh and S. Takahashi, J. Chem. Soc, Chem. Commun. 1986, 1412.
Y. Kamitori, M. Hojo, R. Masuda, T. Izumi and T. Inoue, Synthesis 1983, 387.
B.C. Ranu and A.R. Das, J. Org. Chem. 1991, 56, 4796.
P.A. Risbood and D.M. Ruthven, J. Org. Chem. 1979, 44, 3969.
Y. Kamitori, M. Hojo, R. Masuda, T. Inoue and T. Izumi, Tetrahedron Lett. 1983, 24, 2575.
Y. Kamitori, M. Hojo, R. Masuda, T. Inoue and T. Izumi, Tetrahedron Lett. 1982, 23, 4585.
S. Singh and S. Dev, Tetrahedron 1993, 49, 10959.
F. Hodosan and N. Serban, Rev. Roumaine. Chim. 1969, 14, 121.
A.K. Sinhababu and R.T. Barchardt, Tetrahedron Lett., 1983, 24, 227.
Y. Izumi, H. Nanami, K. Higuchi and M. Onaka, Tetrahedron Lett. 1991, 32, 4741.
M. Onaka, K. Higuchi, H. Nanami and Y. Izumi, Bull. Chem. Soc. Jpn. 1993, 66, 2638.
N.Y.M. Fung, P. De Mayo, J.H. Schauble and A.C. Weedon, J. Org. Chem. 1978, 43, 3977.
J.-M. Lalancette, G. Rollin and P. Dumas, Can. J. Chem. 1972, 50, 3058.
M. Contento, D. Savoia, C. Trombini and A. Umani-Ronchi, Synthesis 1979, 30.
H.O. House, Modern Synthetic Reactions, W.A. Benzamin Inc., Menlo Park, California, 1972.
F.A. Corey and R.J. Sundberg, Advanced Organic Chemistry: Part B, Plenum Press, 1977.
M. Hudlicky, Reactions in Organic Chemistry, Ellis Horwood Ltd., Chichester, 1984.
B.C. Ranu and A.R. Das, J. Chem. Soc, Chem. Commun. 1990, 1334.
M. Fujii, K. Kawaguchi, K. Nakamura and A. Ohno, Chem. Lett. 1992, 1493.
M. Fujii, T. Aida, M. Yoshihara and A. Ohno, Bull. Chem. Soc. Jpn. 1989, 62, 3845.
K. Nakamura, M. Fujii, S. Oka and A. Ohno, Tetrahedron Lett. 1984, 25, 3983.
T. Nishiguchi and F. Asano, J. Org. Chem. 1989, 54, 1531.
A. Cornells and P. Laszlo, Synthesis 1980, 849.
N.A. Noureldin and D.G. Lee, Tetrahedron Lett. 1981, 22, 4889.
V. Balogh, M. Fetizon and M. Golfier, J. Org. Chem. 1971, 36, 1339.
A. McKillop and D.W. Young, Synthesis 1979, 401.
J.M. Melot, F. Taxier-Boullet and A. Foucaud, Tetrahedron 1988, 44, 2215.
M. Fetizon and P. Mourgues, Tetrahedron 1974, 30, 327.
M. Fetizon and P. Mourgues, Tetrahedron 1973, 29, 2867.
A. McKillop and D.W. Young, Synthesis 1979, 481.
A. Esprosito, C. Neri and F. Buonomo, J. Synth. Meth. 1984, 10, 76299z.
N. Herron and CA. Tolman, J. Am. Chem. Soc. 1987, 109, 2837.
Z. Cohen, E. Keinan, Y. Mazur and T.H. Varkony, J. Org. Chem. 1975, 40, 2141.
A.H. Jackson, K.R.N. Rao and E. Smeaton, Tetrahedron Lett. 1989, 30, 2673.
B.R. Chhabra, K. Hayano, T. Ohtsuka, H. Shirahama and T. Matsumoto, Chem. Lett. 1981, 1703.
E. Adelakun, A.H. Jackson, N.S. Ooi and K.R.N. Rao, Tetrahedron Lett. 1984, 25, 6049.
E.C. Taylor, C-S. Chiang, A. McKillop and J.F. White, J. Am. Chem. Soc 1976, 98, 6750.
M.A. Camblor, A. Corma, A. Martinez and J. Perez-Priente, J. Chem. Soc., Chem. Commun. 1992, 589.
N. Herron, G.D. Stucky and C.A. Tolman, J. Chem. Soc, Chem. Commun. 1986, 1521.
J.M. Adams, J.A. Ballantine, S.H. Graham, R.J. Laub, J.H. Purnell, P.I. Reid, W.Y.M. Shamen and J.M. Thomas, Angew. Chem. Int. Ed. Eng. 1978, 17, 282.
S. Hoyer, P. Laszio, M. Orlovic and E. Polla, Synthesis 1986, 655.
M. Nomura and Y. Fujihara, Nippon Kaguku Kaishi 1983, 1818
M. Nomura and Y. Fujihara, CA: 100, 192083g
M. Nomura and Y. Fujihara, Yukagaku 1983, 32, 234
M. Nomura and Y. Fujihara, CA: 99, 53990y.
S.L. Regen, Angew. Chem. Int. Ed. Eng. 1979, 18, 421.
K. Smith, Bull. Chim. Soc. Fr. 1989, 2, 272.
K. Smith and K. Fry, J. Chem. Soc, Chem. Commun. 1992, 187.
T. Ando, J. Yamawaki, T. Kawate, S. Sumi, T. Hanafusa, Bull. Chem. Soc. Jpn. 1982, 55, 2504.
D.E. Bergbreiter and J. Lalonde, J. Org. Chem. 1987, 52, 1601.
M.E. Alonso and A. Morales, J. Org. Chem. 1980, 45, 4530.
M. Onaka, R. Ohno and Y. Izumi, Tetrahedron Lett. 1989, 30, 747.
M. Onaka, T. Mimura, R. Ohno and Y. Izumi, Tetrahedron Lett. 1989, 30, 6341.
P.D. Halphen and T.C. Owen, J. Org. Chem. 1973, 38, 3507.
M. Kodomari, G. Saitoh and S. Yoshitomi, Bull. Chem. Soc. Jpn. 1991, 64, 3485.
H. Parlar and R. Baumann, Angew. Chem. Int. Ed. Eng. 1981, 20, 1014.
G. Hondrogiannis, R.M. Pagni, G.W. Kabalka, P. Anosike and R. Kurt, Tetrahedron Lett. 1990, 31, 5433.
G.W. Kabalka, R.M. Pagni, S. Bains, G. Hondrogiannis, M. Plesco, R. Kurt, D. Cox and J. Green, Tetrahedron Assym. 1991, 2, 1283.
P. Laszlo and J. Luchetti, Tetrahedron Lett. 1984, 25, 4387.
S. Torna, P. Elecko, J. Gazova and F. Salcaoniova, Collect. Czech. Chem. Commun. 1987, 52, 391
S. Torna, P. Elecko, J. Gazova and F. Salcaoniova, CA: 109, 37937f.
P. Laszlo and J. Luchetti, Tetrahedron Lett. 1983, 24, 1901.
P. Laszlo and H. Moison, Chem. Lett. 1989, 1031.
Y.V.S. Narayana Murthy and C.N. Pillai, Synth. Commun. 1991, 21, 783.
V.M. Andreev, L.D. Kwacheva and L.A. Kheifits, Khim.-Farm. Zh. 1992, 26, 68
V.M. Andreev, L.D. Kwacheva and L.A. CA: 116, 255820y.
F. Berree, E. Marchand and G. Morel, Tetrahedron Lett. 1992, 33, 6155.
J. Cabral, P. Laszlo and M.T. Montaufier, Tetrahedron Lett. 1988, 29, 547.
W. Sato, N. Ikeda and H. Yamamoto, Chem. Lett. 1982, 141.
L. Novak, L. Poppe and C. Szantay, Synthesis 1985, 939.
L.C Sams, T.A. Reams and M.A. Durrane, J. Org. Chem. 1978, 43, 2273.
S.S. Yemul, H.B. Kagan and R. Setton, Tetrahedron Lett. 1980, 21, 277.
Y. Kamitori, M. Hojo, R. Masuda, T. Kimura and T. Yoshida, J. Org. Chem. 1986, 51, 1427.
B. Labiad and D. Villemin, Synthesis 1989, 143.
H. Mori, T. Yamazaki, S. Ozawa and Y. Ogino, Bull. Chem. Soc. Jpn. 1993, 66, 2498.
K.H. Patney, Synth. Commun. 1993, 23, 1526.
G. Rosini, R. Galarini, E. Marotta and P. Righi, J. Org. Chem. 1990, 55, 781.
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Smith, K., Fry, C.V., Tzimas, M. (1995). The use of solid supports and supported reagents in liquid phase organic reactions. In: Clark, J.H. (eds) Chemistry of Waste Minimization. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0623-8_4
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