Chiroptical properties of the ketene and diazo chromophores. Part 2.1 Dissymmetric perturbing influence of α-alkyl substituents on the n-π* transitions in cyclic dialkylketenes and 2-diazoalkanes vs. cyclic ketones

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 5, 1999, Pages 1035-1041

  Shustov, Gennady V ^a   Sun, Fang ^a   Sorensen, Ted S ^a   Rauk, Arvi ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043283318     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807591c     Document Type: Article

References (30)

1. Part 1, G. V. Shustov, F. Sun, T. S. Sorensen and A. Rauk, J. Org. Chem., 1998, 63, 661.
2. (a) The Chemistry of Ketenes, Allenes, and Related Compounds, Parts 1, 2, ed. S. Patai, John Wiley & Sons, Inc., New York, 1982;
3. (b) T. T. Tidwell, Ketenes, John Wiley & Sons, Inc., New York, 1995.
4. (a) M. Regitz and G. Maas, Diazo Compounds, Properties and Synthesis, Academic Press, Inc., New York, 1986;
5. (b) H. Zollinger, Diazo Chemistry 1 and 2, VCH Publishers, New York, 1994.
6. (a) J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, Prentice-Hall, Englewood Cliffs, NJ, 1971;
7. (b) R. E. Gawley and J. Aube, Principles of Asymmetric Synthesis, Pergamon Press, Oxford, UK, 1996.
8. (a) M. Legrand and M. J. Rougier, in Stereochemistry. Fundamentals and Methods. Vol. 2: Determination of Configurations by Dipole Moments, CD or ORD, ed. H. B. Kagan, George Thieme, Stuttgart, 1977;
9. (b) D. N. Kirk, Tetrahedron, 1986, 42, 777;
10. D. A. Lightner, in Circular Dichroism. Principles and Applications, eds. K. Nakanishi, N. Berova and R. Woody, VCH Publishers, Inc., New York, 1994.
11. (a) D. E. Bays, G. W. Cannon and R. C. Cookson, J. Chem. Soc. (B), 1966, 885;
12. (b) C. Coulombeau and A. Rassat, Bull. Soc. Chim. Fr., 1966, 3752;
13. C. Coulombeau and A. Rassat, Bull. Soc. Chim. Fr., 1971, 516.
14. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, U. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN94 (Revision E.2). Gaussian, Inc., Pittsburgh, PA, 1995.
15. S. Manabe and C. Nishino, J Chem. Ecol., 1983, 9, 433.
16. D. N. Harpp, L. Q. Bao, C. J. Back, J. G. Gleason and R. A. Smith, J. Org. Chem., 1975, 40, 3420.
17. A. D. Allen and T. T. Tidwell, J. Am. Chem. Soc., 1987, 109, 2774.
18. W. Kirmse and W. Spaleck, Ange. Chem., 1981, 93, 791.
19. A. I. Meyers, D. R. Williams, G. W. Erickson, S. White and M. Druelinger, J. Am. Chem. Soc., 1981, 103, 3081.
20. E. J. Corey and M. A. Tius, Tetrahedron Lett., 1989, 21, 3535.
21. A. P. Masters and T. S. Sorensen, Tetrahedron Lett., 1989, 30, 5869.
22. D. H. R. Barton, F. S. Guziec, Jr. and I. Shahak, J. Chem. Soc., Perkin Trans. 1, 1974, 1794.
23. S. D. Perera, B. L. Shaw and M. Thornton-Pett, J. Chem. Soc., Dalton Trans., 1994, 713.
24. K. Nakagawa, R. Konaka and T. Nakata, J. Org. Chem., 1962, 27, 1597.
25. A. Krebs. W. Rüger, B. Ziegenhagen, M. Hebold, I. Hardtke, R. Müller, M. Schütz, M. Wietzke and M. Wilke, Chem. Ber., 1984, 117, 277.
26. J. P. Flament and H. P. Gervais, Theor. Chim. Acta, 1982, 61, 149.
27. M. F. Ruiz-Lopez and D. Rinaldi, Chem. Phys., 1984, 86, 367.
28. M. F. Ruiz-Lopez, D. Rinaldi and J. L. Rivail, Chem. Phys. 1986. 110, 403.
29. H. Tokiwa and M. Kamiya, J. Mol. Struct. (THEOCHEM), 1988, 181, 25.
30. D. N. Kirk, J. Chem. Soc., Perkin Trans. 1, 1977, 2122.