Cycloaddition of (E)-1-(Phenylseleno)-2-(trimethylsilyl)ethene. Novel Cyclopropane Ring Formation by a 1,2-Shift of a Trimethylsilyl Group

Article abstract of DOI:10.1021/jo00027a003

Reaction of (E)-1-(phenylseleno)-2-(trimethylsilyl)ethene (1) with vinyl ketones 2a-d in the presence of SnCl4 gave cyclopropane products by a formal <2 + 1> cycloaddition accompanied by 1,2-silicon migration rather than <2 + 2> cycloaddition.