Electrochemistry of polyhalogenated organic compounds—II. Electrochemical reduction of 2,2,2-trichloro-1-phenylethyl derivatives

✍ Scribed by A. Merz

• Publisher: Elsevier Science
• Year: 1977
• Tongue: English
• Weight: 357 KB
• Volume: 22
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(77)87008-4

✦ Synopsis

The electroreduction of 2,2,2-trichloro-l-phenylethyl derivatives (VIII) in aqueous dmf yields fl,&dichlorostyrene (VII) and/or the corresponding 2,2-dichloro-1-phenylethyl derivatives (IX). For the set of compounds thus far investigated, there is a strong dependence: ot the product distribution as well as the polarographic halE-wave potentials, on the nature of the substituent adjacent to the trichloromethyl group. These relationships are discussed in terms of a reduction mechanism which shifts from a carhanion model to a concerted elimination depending on an increase in leaving group tendency of this substituent.