Trimethylsilylated 1,3-dienes or styrenes from the reaction between trimethylsilyldiazomethane and vinyl or aryl ketenes

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 847-848

  Léost, Françoise ^a   Doutheau, Alain ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

Cyclopropanones; Decarbonylation; Diazo compounds; Ketenes

Indexed keywords

ACETONE; CYCLOPROPANONE; DIAZOMETHANE; KETENE DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033613762     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02536-2     Document Type: Article

References (22)

1. a) Schaafsma, S.E.; Steinberg, H.; de Boer, Th. J. Reel. Trav. Chim. Pays-Bas 1966, 85, 1170-1172.
2. b) Turro, N.J. Acc. Chem. Res. 1969, 2, 25-32.
3. For the formation of cyclopentenones from intermediate species which can be formally considered as vinyl-cyclopropanones see: a) Grimaldi, J.; Bertrand, M. Tetrahedron Lett. 1969, 3269-3272
4. b) Kim, S.J.; Cha, J.K. Tetrahedron Lett. 1988, 29, 5613-5616.
5. c) Erden, I.; Xu, F-P.; Drunimond, J.; Alstad, R.J. Org. Chem. 1993, 58, 3611-3612.
6. Frey. J.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 1161-1162.
7. a) Rende, A.S. Chem. Ind. (London) 1956, 1053-1054.
8. b) Yates, P.; Abrams, G.D.; Betts, M.J.; Goldstein, S. Can J. Chem. 1971, 49, 2850-2860.
9. Brady, W.T.; Cheng, T.C. J. Organomet. Chem. 1977. 137, 287-292.
10. a) Collomb, D.; Deshayes, C.; Doutheau, A. Tetrahedron 1996, 52, 6665-6684.
11. b) Collomb, D.; Chantegrel, B.; Deshayes, C. Tetrahedron 1996, 52, 10455-10472.
12. c) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 38, 1397- 1398.
13. d) Léost, F.; Chantegrel, B.; Deshayes, C. Tetrahedron 1997, 53, 7557-7576; 1998, 54, 6457-6474.
14. d) Léost, F.; Chantegrel, B.; Deshayes, C. Tetrahedron 1997, 53, 7557-7576; 1998, 54, 6457-6474.
15. For the reaction between trimethylsilyldiazomethane and silylated biskelenes see: Colomvakos, J.D.; Egle, I; Ma, J.; Pole, D.L.; Tidwell, T.T.; Warkentin, J. J. Org. Chem. 1996, 61, 9522-9527.
16. 13C NMR spectra.
17. This compound was prepared from diphenylacetic chloride: Taylor, E.C.; McKillop, A.; Hawks, G.H. Organic Syntheses Ed Wiley New-York, 1988, vol VI, pp 549-551.
18. Desilylation occured during column chromatography.
19. Wasserman, H.H.; Berdahl, D.R.; Lu, T.J. The chemistry of cyclopropanones in Rappoport, Z., Ed. The Chemistry of the Cyclopropyl Group Wiley: New York, 1987, pp 1455-1532.
20. a) Hayes, D.M.; Zeiss, C.A.; Hoffmann, R.J. Phys. Chem. 1971, 75, 340-344.
21. b) Büchi, G.; Hochstrasser, U.; Pawlak, W.J. Org. Chem. 1973, 38, 4348-4350 and references cited therein.
22. Rhodium acetate did not interfere in the decarbonylation of the cyclopropanone since diene 8d was formed in a similar yield from the ketene 7d obtained by the thermolysis of diazo 6d in refluxing toluene without catalyst.