Reaction of sterically congested thiones with benzyne. The first isolation of a thioaldehyde–benzyne adduct

Abstract

Reaction of 2,4,6-tri-tert-butylthiobenzaldehyde (3) with benzyne prepared from phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate (1) and tetrabutylammonium fluoride afforded 5,7-di-tert-butyl-3,3-dimethylindan-1-yl phenyl sulfide (5) in 92% yield, whereas a [2 + 2] cycloadduct and an ene-reaction product were obtained by the reaction of sterically congested aliphatic thiones with benzyne.