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Volumn 127, Issue 4, 2005, Pages 1201-1205

Intramolecular [2 + 2] photocycloaddition/thermal fragmentation: Formally "allowed" and "forbidden" pathways toward 5-8-5 ring systems

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BUTANE; CHEMICAL BONDS; COMPLEXATION; MOLECULAR DYNAMICS; THERMOANALYSIS;

EID: 13644271604     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044542i     Document Type: Article
Times cited : (20)

References (45)
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    • For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
    • (1986) J. Chem. Soc., Perkin Trans. 1 , pp. 291-297
    • Mehta, G.1    Reddy, A.V.2    Srikrishna, A.3
  • 29
    • 0034644425 scopus 로고    scopus 로고
    • For examples of related cycloaddition/fragmentations, see: (c) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (f) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (g) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (h) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (i) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 325-331. (j) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (k) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (l) Mehta, G.; Reddy, A. V.; Srikrishna, A. J. Chem. Soc., Perkin Trans. 1 1986, 291-297. (m) White, J. D.; Kim, J.; Drapela N. E. J. Am. Chem. Soc. 2000, 122, 8665.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8665
    • White, J.D.1    Kim, J.2    Drapela, N.E.3
  • 32
    • 0029825282 scopus 로고    scopus 로고
    • For the preparation of related cycloadducts, see: (b) Limanto, J.; Tallarico, J. A.; Porter, J. R.; Khuong, S. K.; Houk, K. N.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 14748-14758. (c) Tallarico, J. A.; Randall, M. L.; Snapper, M. L. J. Am. Chem. Soc. 1996, 118, 9196-9197.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9196-9197
    • Tallarico, J.A.1    Randall, M.L.2    Snapper, M.L.3
  • 37
    • 13644270051 scopus 로고    scopus 로고
    • note
    • 2O at room temperature under Ar atmosphere for 1 days.
  • 38
    • 0000478319 scopus 로고
    • For a review, see: Shapiro, R. H. Org. React. 1976, 23, 405-423.
    • (1976) Org. React. , vol.23 , pp. 405-423
    • Shapiro, R.H.1
  • 39
    • 13644264455 scopus 로고    scopus 로고
    • Purchased from Aldrich Chemical Co.
    • Purchased from Aldrich Chemical Co.
  • 40
    • 13644252714 scopus 로고    scopus 로고
    • note
    • With 50% yield based on 50% conversion.
  • 42
    • 13644250398 scopus 로고    scopus 로고
    • note
    • 1H NMR on the crude reaction mixture.
  • 43
    • 13644258762 scopus 로고    scopus 로고
    • note
    • While the fragmentations are likely to proceed through biradical intermediates, the terms symmetry-allowed and symmetry-forbidden are used to describe the stereochemical changes occurring between the fused cyclobutane starting materials and the corresponding cyclooctadiene products.


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