Stereospecific ring contractions of 7-chlorobicyclo[3.2.0]hept-2-en-6-ones and equilibration studies of 7-alkylbicyclo[3.2.0]hept-2-en-6-ones

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1974, Pages 927-932

  Brook, Peter R ^a   Duke, A Jonathan ^a   Harrison, John M ^a   Hunt, Keith ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049137855     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19740000927     Document Type: Article

References (22)

1. Preliminary communication, P. R. Brook, J. M. Harrison, and A. J. Duke, Chem. Comm., 1970, 589.
2. R. B. Woodward and R. Hoffmann, Angew. Chem. Internat. Edn., 1969, 8, 847.
3. W. T. Brady and R. Roe, J. Amer. Chem. Soc., 1970, 92, 4618;
4. W. T. Brady and E. F. Hoff, J. Org. Chem., 1970, 35, 3733, and references cited in these papers.
5. M. Rey, S. Roberts, A. Dieffenbacher, and A. S. Dreiding, Helv. Chim. Acta, 1970, 53, 417.
6. T. DoMinh and O. P. Strausz, J. Amer. Chem. Soc., 1970, 92, 1766.
7. J. M. Conia and J. Salaun, Accounts Chem. Res., 1972, 5, 37.
8. J. Meinwald, S. S. Labone, and M. S. Chadha, J. Amer. Chem. Soc., 1963, 85, 582.
9. W. T. Brady and J. P. Hieble, J. Amer. Chem. Soc., 1972, 94, 4278.
10. P. R. Brook and J. M. Harrison, J.C.S. Chem. Comm., 1972, 997.
11. D. L. Garin and K. L. Canmalk, J.C.S. Chem. Comm., 1972, 333;
12. P. D. Bartlett and T. Ando, J. Amer. Chem. Soc., 1970, 92, 7518;
13. W. T. Brady and J. P. Hieble, J. Org. Chem., 1971, 36, 2033.
14. Zinc-acetic acid has also been used: for a brief report see M. Rey, U. A. Hüber and A. S. Dreiding, Tetrahedron Letters, 1968, 3583.
15. For other examples of dehalogenation with this reagent see I. T. Borowitz, K. C. Kirby, and R. Wirkhaus, J. Org. Chem., 1966, 31, 4031.
16. This reaction has been reported earlier: S.A. p. 6,706,947/1968 (Chem. Abs., 1968, 70, 106,068).
17. P. R. Brook, A. J. Duke, and J. R. C. Duke, Chem. Comm., 1970, 574.
18. Albert Roussel, D.Sc. Thesis, Université Catholique de Louvain, 1970. We thank Professor Ghosez for a copy of this thesis.
19. See for example refs. 1, 3, and 4; and also for comments on a ‘masochistic steric effect,’ B. M. Jacobson and P. D. Bartlett, J. Org. Chem., 1973, 38, 1036.
20. P. R. Brook and A. J. Duke, J.C.S. Perkin I, 1973, 1013.
21. The method of R. H. Horn, R. B. Miller, and S. N. Slater, J. 1950, 2900.
22. B. T. Brooks and G. Wilbert, J. Amer. Chem. Soc., 1941, 63, 870.