Fragmentation of 2, 2, 2-Triphenylethoxychlorocarbene: Evidence for Ultrafast Fragmentation-Rearrangement in Excited Diazirines

X Fu, RA Moss, P Piotrowiak, M Myahkostupov…

Index: Fu, Xiaolin; Moss, Robert A.; Piotrowiak, Piotr; Myahkostupov, Mykhaylo; Gould, Ian R. Organic Letters, 2006 , vol. 8, # 21 p. 4807 - 4809

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Citation Number: 4

Abstract

Photolysis of 3-(2, 2, 2-triphenylethoxy)-3-chlorodiazirine gives 2, 2, 2- triphenylethoxychlorocarbene which fragments with 1, 2-phenyl migration and loss of CO and Cl-to yield the 1, 1, 2-triphenylethyl cation and thence 1, 1, 2-triphenylethene by proton loss. However, ps and fs laser flash photolysis provides evidence that up to 25% of the alkene product stems from carbocation that arises directly from excited diazirine rather ...