On the reaction of alcohols with halocarbenes. Are carbocations intermediates?

✍ Scribed by Igor R. Likhotvorik; Maitland Jones Jr.; Alexander G. Yurchenko; Pavel A. Krasutsky

• Book ID: 104244569
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 219 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93454-9

✦ Synopsis

There is no evidence for hydrfde shift in the reaction of WhoIs 1 and 2 with dchbrocarbene.

Accordingly, the intermedate cannot be a free catbocation. It is suggested that the pmducts are formed through a cotnttinatfon of SNi and direct dispketnent reactfons in which tfght bn pairs are involved.

JACK HINE and his coworkers, in 1953, suggested that chbroalkoxycartrenes were intermediates in the reactbns of alcohols wfth akall and habforms? They favored a p elimination giving the observed alkene, carbon monoxide and halide.