Stereoselective isomerisations of 4-(2′,5′-dimethoxyphenyl)-2,5-dimethyl-1,3-dioxolanes and their 2′-chloro-5′-methoxyphenyl analogues. Temperature-dependent diastereoselective formation of isochromanes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 22, 1997, Pages 3361-3370

  Giles, Robin G F ^a   Rickards, Rodney W ^b   Senanayake, Badra S ^a,b  

^a MURDOCH UNIVERSITY   (Australia)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748717119     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704543c     Document Type: Article

References (21)

1. R. G. F. Giles, R. W. Rickards and B. Senanayake, J. Chem. Soc., Perkin Trans. 1, 1996, 2241.
2. (a) R. H. Thomson, Naturally Occurring Quinones, Academic Press, London, 1971;
3. (b) R. H. Thomson, Naturally Occurring Quinones III, Recent Advances, Chapman and Hall, London, 1987;
4. (c) R. H. Thomson, Naturally Occurring Quinones IV, Recent Advances, 4th edn., Blackie Academic and Professional, Chapman and Hall, London, 1997.
5. D. W. Cameron, R. I. T. Cromartie, D. G. I. Kingston and Lord Todd, J. Chem. Soc., 1964, 51.
6. R. G. F. Giles, V. R. Lee Son and M. V. Sargent, Aust. J. Chem., 1990, 43, 777.
7. (a) V. VanRheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 1973;
8. (b) R. Ray and D. S. Matteson, Tetrahedron Lett., 1980, 21, 449.
9. G. Casiraghi, M. Cornia and G. Rassu, J. Org. Chem., 1988, 53, 4919.
10. M. K. Meilahn, C. N. Statham, J. L. McManaman and M. E. Munk, J. Org. Chem., 1975, 40, 3551.
11. A. Bhati, J. Chem. Soc., 1963, 730.
12. T. Kometani, Y. Takeuchiand E. Yoshii, J. Chem. Soc., Perkin Trans. 1, 1981, 1197.
13. R. G. F. Giles, I. R. Green, V. I. Hugo, P. R. K. Mitchell and S. C. Yorke, J. Chem. Soc., Perkin Trans. 1, 1983, 2309.
14. D. W. Cameron, D. G. I. Kingston, N. Sheppard and Lord Todd, J. Chem. Soc., 1964, 98.
15. R. G. F. Giles, I. R. Green, V. I. Hugo, P. R. K. Mitchell and S. C. Yorke, J. Chem Soc., Perkin Trans. 1, 1984, 2383.
16. M. Karplus, J. Chem. Phys., 1960, 33, 1842.
17. P. A. Bartlett, W. S. Johnson and J. D. Elliott, J. Am. Chem. Soc., 1983, 105, 2088.
18. For a discussion of related effects, see S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089.
19. R. G. F. Giles, I. R. Green, L. S. Knight, V. R. Lee Son and S. C. Yorke, J. Chem. Soc., Perkin Trans. 1, 1994, 865.
20. A. L. J. Beckwith and S. H. Goh, J. Chem. Soc., Chem. Commun., 1983, 907.
21. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.