ON THE REACTION OF ALCOHOLS WITH HALOCARBENES. ARE CARBOCATIONS INTERMEDIATES?
There is no evidence for hydride shift in the reaction of alcohols 1 and 2 with dichlorocarbene.Accordingly, the intermediate cannot be a free carbocation.It is suggested that the products are formed through a combination of SNi and direct displacement reactions in which tight ion pairs are involved.
Likhotvorik, Igor R.,Jones, Maitland,Yurchenko, Alexander G.,Krasutsky, Pavel A.