The Thio-Claisen Rearrangement of Allylic Phenyl Sulfides

The Reaction of Phenolic Compounds with Isoprenoids. (Part V)

Abstract

The thio-Claisen rearrangement of prenyl phenyl sulfide (γ, γ-dimethyl allyl phenyl sulfide) (1a) gave 2-isopropyl-1-thiacoumaran (2), 2, 2-dimethyl-1-thiachroman (3) and 3-methyl-1-butenyl phenyl sulfide (4).
The similar reactions of β, γ-dimethyl allyl phenyl sulfide (7a) and crotyl phenyl sulfide (12) were also studied.
From these results, the effect of γ-methyl groups of allylic phenyl sulfides on the rearrangement reactions was discussed.