82293-67-2Relevant academic research and scientific papers
Reactions of Haloketenes with Allyl Ethers and Thioethers: A New Type of Claisen Rearrangement
Malherbe, Roger,Rist, Guenther,Bellus, Daniel
, p. 860 - 869 (2007/10/02)
A new reaction of dichloroketene (2) with allylic ethers, sulfides, and selenide 1 has been observed.A sigmatropic rearrangement takes place at room temperature, leading to α,α'-dichloro-γ,δ-unsaturated esters 3.The scope of this reaction was further investigated with dibromoketene (16), difluoroketene (17), electron-deficient chloroketenes, and different allylic systems.In the course of these studies, total syntheses of two naturally occurring macrolides, phoracantholide I and phoracantholide J, were achieved.Medium-ring conformations are discussed.
