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

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

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被引用次数: 22

摘要

(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 ( ...