New imino-wittig rearrangement of benzyl and allyl hydroximates

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9078-9079

  Miyata, Okiko ^a   Koizumi, Tomoko ^a   Ninomiya, Ichiya ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001272032     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961768y     Document Type: Article

References (15)

1. Reviews on the 1,2-Wittig rearrangement: (a) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763. (b) Marshall, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 975-1014.
2. Reviews on the 1,2-Wittig rearrangement: (a) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763. (b) Marshall, J. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 975-1014.
3. A few papers have been published on the migration of alkenyl, carbonyl, and thiocarbonyl groups. (a) Rautenstrauch, V.; Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1974, 96, 2576-2580. (b) Hayashi, T.; Baba, H. J. Am. Chem. Soc. 1975, 97, 1608-1609. (c) Crooks, P. A.; Galt, R. H. B.; Matusiak, Z. S. Chem. Ind. 1976, 693-694. (d) Lee, S. D.; Chan, T. H.; Kwon, K. S. Tetrahedron Lett. 1984, 25, 3399-3402.
4. A few papers have been published on the migration of alkenyl, carbonyl, and thiocarbonyl groups. (a) Rautenstrauch, V.; Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1974, 96, 2576-2580. (b) Hayashi, T.; Baba, H. J. Am. Chem. Soc. 1975, 97, 1608-1609. (c) Crooks, P. A.; Galt, R. H. B.; Matusiak, Z. S. Chem. Ind. 1976, 693-694. (d) Lee, S. D.; Chan, T. H.; Kwon, K. S. Tetrahedron Lett. 1984, 25, 3399-3402.
5. A few papers have been published on the migration of alkenyl, carbonyl, and thiocarbonyl groups. (a) Rautenstrauch, V.; Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1974, 96, 2576-2580. (b) Hayashi, T.; Baba, H. J. Am. Chem. Soc. 1975, 97, 1608-1609. (c) Crooks, P. A.; Galt, R. H. B.; Matusiak, Z. S. Chem. Ind. 1976, 693-694. (d) Lee, S. D.; Chan, T. H.; Kwon, K. S. Tetrahedron Lett. 1984, 25, 3399-3402.
6. A few papers have been published on the migration of alkenyl, carbonyl, and thiocarbonyl groups. (a) Rautenstrauch, V.; Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1974, 96, 2576-2580. (b) Hayashi, T.; Baba, H. J. Am. Chem. Soc. 1975, 97, 1608-1609. (c) Crooks, P. A.; Galt, R. H. B.; Matusiak, Z. S. Chem. Ind. 1976, 693-694. (d) Lee, S. D.; Chan, T. H.; Kwon, K. S. Tetrahedron Lett. 1984, 25, 3399-3402.
7. The Substrates 3a-i and 5a,b,e were prepared according to the reported procedure. Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284-294.
8. 1H-NMR spectra according to ref 5b, which states that signals due to α′-methine protons of cis-O-methyloxime appear at appreciably lower fields than those of trans-isomers.
9. (a) Creary, X.; Wang, Y.-X.; Jiang, Z. J. Am. Chem. Soc. 1995, 117, 3044-3053.
10. (b) Karabatsos, G. J.; Hsi, N. Tetrahedron 1967, 23, 1079-1095.
11. 2a
12. Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron 1994, 50, 5927-5932 and references cited therein.
13. Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375-377.
14. Lansbury, P. T.; Pattison, V. A.; Sidler, J. D.; Bieber J. B. J. Am. Chem. Soc. 1966, 88, 78-84.
15. We could not isolate cyclopentanone O-methyloxime as a product that is expected to be formed via radical cyclization of an intermediary imidoyl radical D in the reaction of 3i.