Ring Contraction by Rearrangement of a β-Chloro Sulfide - American

REYNOLD C. FUSON AND A. JOHN SPEZIALE

1582

Vol. 71

[CONTRIBUTIONFROM THE NOYES CHEMICAL LABORATORY, UNIVERSITY OF ILLINOIS]

Ring Contraction by Rearrangement of a p-Chloro Sulfide B Y REYNOLD c, FUSONAND A.

JOHN

SPEZIALE~

Treatment of certain P-hydroxyisopropyl sulfides with thionyl chloride or hydrochloric acid has been shown to yield not the expected 2-chloroisopropyl sulfides (I) but the corresponding 2chloro-n-propyl sulfides (III).2 It has been postulated that the rearrangement involves a cyclic sulfonium intermediate (11); the 2-chloroisopropyl sulfides, if formed a t all, are likewise intermediates. CHs

[ F ]+ [."