The Journal of Organic Chemistry

Mild generation of alkylidenecarbenes from (tosylazo) alkenes and silylvinyl triflates. Mode of decomposition and nature of the carbene intermediates

DP Fox, JA Bjork, PJ Stang

Index: Fox, Dennis P.; Bjork, Jon A.; Stang, Peter J. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 3994 - 4002

Full Text: HTML

Citation Number: 22

Abstract

(Tosylazo) alkenes, R2C= CHN= NTs, decomposed in olefin-solvent mixtures both under neutral conditions at room temperature and with amine bases present to produce alkylidenecyclopropanes in moderate to good yields. Diazoalkenes, R2C= C= N2, were implicated as the intermediates leading to alkylidenecarbenes, R2C= C:, in the decompositions. Fluoride-induced a-elimination of trimethylsilyl triflate from (CH3) 2C= C ( ...

Related Articles:

A new preparation of methylenecyclopropanes utilizing trimethylsilyldiazomethane

[Sakai, Atsushi; Aoyama, Toyohiko; Shioiri, Takayuki Tetrahedron, 1999 , vol. 55, # 12 p. 3687 - 3694]

Unsaturated carbenes from primary vinyl triflates. I. Method and scope

[Stang,P.J. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 4562 - 4569]

Alkylidenecarbenes

[Tanabe,M.; Walsh,R.A. Journal of the American Chemical Society, 1963 , vol. 85, p. 3522 - 3523]

Unsaturated carbenes from primary vinyl triflates. I. Method and scope

[Stang,P.J. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 4562 - 4569]

New reaction sequence leading to the formation of unsaturated carbenes

[Newman,M.S.; Din,Z.U. Journal of Organic Chemistry, 1973 , vol. 38, p. 547 - 549]

More Articles...