A new oxidativesubstitutionreaction where an organotin group is replaced by an acetoxy group has been investigated; this reaction has been successfully applied to the synthesis of 4-ylidenebutenolides.
Photochemical Generation of Radical Species from<i>α</i>-Stannyl Ethers and Their Reaction with Conjugate Enones
作者:Tetsuhiro Mikami、Manabu Harada、Koichi Narasaka
DOI:10.1246/cl.1999.425
日期:1999.5
Photochemical reaction of α-stannyl ethers and conjugated enones proceeds in the presence of photosensitizers to give addition products of aryloxymethyl radicals to the enones.
Although the [2,3]-Wittig and Wittig-Still rearrangements have long been known, their application in the generation of quaternary carbon centers in carbocyclic ring systems is sparse. Model studies utilizing this strategy and possible mechanisms are discussed herein. Unprecedented examples of an a-elimination pathway from stannylmethyl allyl ethers as a major undesired product in some Wittig-Still rearrangements are reported.