An easy access to trisubstituted vinyl chlorides and improved synthesis of chloro/bromostilbenes

Tetrahedron

Volumn 54, Issue 47, 1998, Pages 14315-14326

  Muthiah, C ^a   Kumar, K Praveen ^a   Kumaraswamy, Sudha ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

STILBENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0032211326     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00886-2     Document Type: Article

References (15)

1. 1. Kumaraswamy, S.; Kumara Swamy, K. C. Tetrahedron Lett. 1997, 38, 2183.
2. 2. a) Crenshaw, M. D.; Zimmer, H. J. Org. Chem. 1983, 48, 2782.
3. b) Tsai, H. J. Tetrahedron Lett. 1996, 37, 629.
4. 3. a) Petrova, J.; Coutrot, P.; Drefux, M.; Savignac, P. Synthesis 1975, 658.
5. 4, but removal of by-products is not very convenient in case of non-volatile phosphonates.)
6. c) Morise, X.; Savignac, P.; Denis, M. J. Chem. Soc., Perkin Trans. I 1996, 2179.
7. 4 Kumaraswamy, S.; Selvi, R. S.; Kumara Swamy, K. C. Synthesis 1997, 207.
8. 5. Even in the synthesis of fluoro-olefins (ref. 2b) and 1 -chlorovinyl sulfoxides by the Horner-Wadsworth reaction, a more expensive base, LDA is used Otten, P. A.; Davies, H. M.; van der Gen, A. Tetrahedron Lett. 1995, 36, 781.
9. 6. Larsen, R. O.; Aksnes, G. Phosphorus Sulfur 1983, 16, 339.
10. 7. Desiraju, G. R.; Sarma, J. A. R. P. Proc. Indian Acad. Sci. (Chem. Sci.) 1986, 96, 599.
11. 8. A similar result was obtained by Zimmer, et al. Zimmer, H.; Hickey, K. R., Schumaker, R. J. Chimia 1974, 28, 656.
12. 3 as a base in the Horner-Wadsworth reaction is reported, it has not been used for the synthesis of chlorostilbenes. See Texier-Boulett, F.; Foucaud, A. Synthesis 1979, 884.
13. 10. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, Pergamon, Oxford, 1986.
14. 11. Sioda, R. E.; Cowan, D. O.; Koski, W. S. J. Am. Chem. Soc. 1967, 89, 230.
15. 12. SHELX-97, A package for structure solution and refinement, Sheldrick, G. M., University of Göttingen, Göttingen, Germany.