Photochemical Doyle-Kirmse Reaction – a Metal-Free Route to Allenes

25 November 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

This report describes metal-free, blue light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yields. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.

Keywords

photochemistry proceeds
diazocompouds
the Doyle-Kirmse reaction
allenes

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