Thermal and electron transfer induced reactions of enediynes and enyne-allenes, 5: First isolation of two rotamers about the P-C bond in a phosphane oxide

Liebigs Annales

Volumn , Issue 4, 1997, Pages 733-736

  Schmittel, Michael ^a   Kiau, Susanne ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Benzofulvenes; Cyclizations; Enyne allenes; Rotamers; Semiempirical calculations

Indexed keywords

EID: 0345333611     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970415     Document Type: Article

References (17)

1. [1a] M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975-4978.
2. [1b] M. Schmittel, M. Strittmatter, K. Vollmann, S. Kiau, Tetrahedron Lett. 1996, 37, 999-1002.
3. M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. 1996, 108, 1952-1954;
4. Angew. Chem. Int. Ed. Engl. 1996, 35, 1843-1845.
5. [3a] F. Fringuelli, A. Taticchi, Dienes in the Diels-Alder Reaction, John Wiley & Sons, New York 1990, 158-159.
6. [3b] W. B. Mannung, T. P. Kelly, G. M. Muschik, J. Org. Chem. 1980, 45, 2535-2536.
7. [3c] B. I. Rosen, W. P. Fischer, J. Org. Chem. 1977, 42, 3464.
8. [3d] Y.-C. Lai, S. E. Mallakpour, G. B. Butler, J. Org. Chem. 1985, 50, 4378-4381.
9. R. Brückner, R. Huisgen, J. Schmid, Tetrahedron Lett. 1990, 31, 7129-7132.
10. [5a] L. Pogliani, D. Viterbo, M. Giannini, M. Ceruti, P. Ugliengo, Gazz. Chim. Ital. 1991, 121, 81-88.
11. [5b] S. B. Bulgarevich, V. L. Goncharova, P. N. Kozachenko, A. M. Shvets, O. A. Ozipov, Zh. Structr. Khim. 1981, 157-159.
12. [5c] A. M. Panov, G. V. Ratvskii, V. I. Dmitriev, Zh. Obsch. Khim. 1983, 53, 1670-1671.
13. M. Schmittel, M. Keller, S. Kiau, M. Strittmatter, Chem. Eur. J., submitted for publication.
14. 6. After cooling to room temperature, sharp signals and no change in the ratio of red-4d and yellow-4d could be detected. Hence, the coalescence effect is thought to be caused by a ring inversion process of the 1,3-cyclohexadiene moiety at higher temperatures.
15. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
16. E. Keller, SCHAKAL 92, PC Computer Program, Kristallographisches Institut der Universität Freiburg, 1992.
17. Tripos Inc., "Sybyl 6.3", Molecular Silverware, Rohm and Haas Company, 1996.