The unusual formation of methyl α-(5,6-dimethoxycarbonyl-2,3-dimethoxyazepin-7-ylidene)-α-[5- methoxycarbonyl-2,3-dimethoxypyrid-6-ylacetate during the pyrolysis of "azido-meta-hemipinate": First example of a reaction involving a concomitant ring expansion and ring extrusion

Journal of Heterocyclic Chemistry

Volumn 33, Issue 4, 1996, Pages 1333-1337

  Eswaran, S V ^a   Neela, H Y ^b   Ramakumar, S ^b   Viswamitra, M A ^b  

^a UNIVERSITY OF DELHI   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0142015882     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330454     Document Type: Article

References (20)

1. [1a] E. F. V. Scriven and K. Turnbull, Chem. Rev., 88, 297 (1988);
2. [b] P. A. S. Smith, in Azides and Nitrenes, E. F. V. Scriven, ed, Academic Press, Orlando, Florida, 1984, pp 95-203;
3. [c] B. Iddon, O. Meth-Cohn, E. F. V. Scriven, H. Suschitzky and P. T. Gallagher, Angew. Chem., Int. Ed. Engl., 18, 900 (1979).
4. D. M. Barnes, Science, 234, 15 (1986).
5. L. K. Dyall and J. K. Kemp, in The Chemistry of Functional Groups, Suppl. D., S. Patai and Z. Rappoport, eds, John Wiley, 1983, pp 287-320.
6. J. H. Hall, F. E. Behr and R. L. Reed, J. Am. Chem. Soc., 94, 4952 (1972).
7. P. A. S. Smith, G. F. Budde and S. S. P. Chou, J. Org. Chem., 50, 2062 (1985).
8. R. Purvis, R. K. Smalley, W. A. Struchan, H. Suschitzky, J. Chem. Soc., Perkin Trans I, 191 (1978).
9. R. E. Banks and A. Prakash, Tetrahedron Letters, 99, (1973); R. E. Banks, N. D. Venayak and T. A. Hamor, J. Chem. Soc., Chem. Commun., 900 (1980).
10. R. E. Banks and A. Prakash, Tetrahedron Letters, 99, (1973); R. E. Banks, N. D. Venayak and T. A. Hamor, J. Chem. Soc., Chem. Commun., 900 (1980).
11. R. J. Sundberg, S. R. Suter and M. J. Brenner, J. Am. Chem. Soc., 94, 513 (1972).
12. R. J. Sundberg, J. Am. Chem. Soc., 88, 3781 (1966).
13. [10a] O. L. Chapman, J. P. LeRoux, J. Am. Chem. Soc., 100, 282 (1978);
14. [b] T. Donnelly, I. R. Dunkin, D. S. D. Norwood, A. Prentice, C. J. Shields and P. C. P. Thomson, J. Chem. Soc., Perkin Trans II, 307 (1985);
15. [c] W. D. Crow and C. Wentrup, Tetrahedron Letters, 6149 (1968).
16. R. A. Abramowitch, S. R. Challand and E. F. V. Scriven, J. Org. Chem., 37, 2705 (1972).
17. D. Cremer and J. A. Pople, J. Am. Chem. Soc., 97, 1354 (1975).
18. T. Ikeda, S. Kanahara and T. Ujjie, Kanazawa Daigaku Yakugakuba Kenkyu Nempô, 8, 1 (1958); Chem. Abstr., 53, 4287 (1959).
19. T. Ikeda, S. Kanahara and T. Ujjie, Kanazawa Daigaku Yakugakuba Kenkyu Nempô, 8, 1 (1958); Chem. Abstr., 53, 4287 (1959).
20. P. Main, S. J. Fiske, S. E. Hull, L. Lessinger, G. Germain, J, P. Declerq, M. M. Woolfson (1980) Multan80. A system of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data, Universities of York, England, and Louvain, Belgium.