Environmentally benign procedures for the preparation and isolation of 3-methylcyclopent-2-en-1-one

Australian Journal of Chemistry

Volumn 50, Issue 9, 1997, Pages 921-925

  Bagnell, Laurence ^a   Bliese, Marianne ^a   Cablewski, Teresa ^a   Strauss, Christopher R ^a   Tsanaktsidis, John ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001640452     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/C97097     Document Type: Article

References (28)

1. Piancatelli, G., D'Auria, F., and D'Onofrio, F., Synthesis, 1994, 867.
2. Gilbert, J. C., and Selliah, R. D., Tetrahedron, 1994, 50, 1651.
3. Petasis, N. A., and Patane, M. A., Tetrahedron Lett., 1990, 31, 6799.
4. Rosini, G., Ballini, R., and Sorrenti, P., Tetrahedron, 1983, 39, 4127.
5. Janssen, C. G. M., Simons, L. H. J. G., and Godefroi, E. F., Synthesis, 1982, 389.
6. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
7. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
8. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
9. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
10. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
11. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
12. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
13. Kishi, N., Mikami, K., and Nakai, T., Tetrahedron, 1991, 47, 8111; Ceccherelli, P., Curini, M., Marcotullio, M. C., Rosati, O., and Wenkert, E., J. Org. Chem., 1990, 55, 311; Mandal, A. K., and Mahajan, S. W., Tetrahedron, 1988, 44, 2293; Liotta, D., Saindane, M., Barnum, C., and Zima, G., Tetrahedron, 1985, 41, 4881; Hendrickson, J. B., and Palumbo, P. S., J. Org. Chem., 1985, 50, 2110; Zhou, Y. F., and Huang, N. Z., Synth. Commun., 1982, 12, 795; Smith, A. B., III, Toder, B. H., Branca, S. J., and Dieter, R. K., J. Am. Chem. Soc., 1981, 103, 1996; Ho, T.-L., J. Chem. Soc., Chem. Commun., 1980, 1149.
14. Acheson, R. M., and Robinson, R., J. Chem. Soc., 1952, 1127.
15. Vogel, A. I., 'Practical Organic Chemistry' 4th Edn, p. 854 (Longmans: New York 1978).
16. Karpinski, M. L., Nicholas, D., and Gilbert, J. C., Org. Prep. Proced. Int., 1995, 27, 569.
17. Jensen, J. L., and Hashtroudi, H., J. Org. Chem., 1976, 41, 3299.
18. Tsuji, J., Yamada, T., Kaito, M., and Mandai, T., Bull. Chem. Soc. Jpn, 1980, 53, 1417.
19. Heathcock, C. H., in 'Comprehensive Organic Synthesis' (Eds B. M. Trost and I. Fleming) Vol. 2 (Ed. C. H. Heathcock) Part 2, p. 133 (Pergamon: New York 1993).
20. Raner, K. D., Strauss, C. R., Trainor, R. W., and Thorn, J. S., J. Org. Chem., 1995, 60, 2456.
21. An, J., Bagnell, L., Cablewski, T., Strauss, C. R., and Trainor, R. W., J. Org. Chem., 1997, 62, 2505.
22. Bagnell, L., Cablewski, T., Strauss, C. R., and Trainor, R. W.; J. Org. Chem., 1996, 61, 7355.
23. Strauss, C. R., and Trainor, R. W., Aust. J. Chem., 1995, 48, 1665.
24. Raner, K. D., and Strauss, C. R., J. Org. Chem., 1992, 57, 6231; Raner, K. D., Strauss, C. R., Vyskoc, F., and Mokbel, L., J. Org. Chem., 1993, 58, 950.
25. Raner, K. D., and Strauss, C. R., J. Org. Chem., 1992, 57, 6231; Raner, K. D., Strauss, C. R., Vyskoc, F., and Mokbel, L., J. Org. Chem., 1993, 58, 950.
26. Cablewski, T., Faux, A. F., and Strauss, C. R., J. Org. Chem., 1994, 59, 3408.
27. Williams, P. J., and Strauss, C. R., J. Sci. Food Agric., 1978, 29, 527; Williams, P. J., Strauss, C. R., Klingner, K. E., Obst, S. R., and Anderson, G. L. G., Food Technol. Aust., 1981, 33(1), 12.
28. Williams, P. J., and Strauss, C. R., J. Sci. Food Agric., 1978, 29, 527; Williams, P. J., Strauss, C. R., Klingner, K. E., Obst, S. R., and Anderson, G. L. G., Food Technol. Aust., 1981, 33(1), 12.