One-Pot Preparation of Crowded Olefins from Hindered Ketones with Alkyllithiums and Thionyl Chloride

Article abstract of DOI:10.1021/jo00267a027

A series of crowded olefins were prepared in high yield by the one-pot reaction of in situ generated lithium alkoxides, formed from hindered ketones and alkyllithiums, with thionyl chloride.The prepared olefins are generally inaccessible by either the Wittig reaction or using Grignard reagents becouse of predominant electron transfer-reduction of hindered ketones.