The fate of bromine formed from C-Br cleavage during the course of anodic oxidation of alkyl bromides in acetonitrile on platinum has been investigated potentiostatically. It is suggested that positive bromine species are formed and they are potentially reactive towards alkyl bromides, yielding similar products to those obtained by direct anodic oxidation of the same bromides. Furthermore, whereas alkyl chlorides do not undergo C-Cl fission by direct anodic oxidation it is shown that positive bromine species are energetically sufficient to break C-Cl bonds, although not very efficiently. We suggest that a possible structure for the complex between acetonitrile and positive bromine species is mainly [(CH3CN)2Br]+Br3- or [CH3CNBr]+Br3- and the mechanism for its formation is discussed. The spectrum of this species found identical to that of Br3- (269 nm) in acetonitrile.
|Number of pages||5|
|Journal||Journal of the Chemical Society. Perkin Transactions 2|
|State||Published - 1 Jan 1981|
ASJC Scopus subject areas
- Chemistry (all)