The reduction of triarylcarbenium ions by alcohols: simple hydride transfer or concerted breakdown of ortho-adducts ?
Huszthy, Péter; Lempert, Károly; Simig, Gyula; Tamás, József
Журнал:
Journal of the Chemical Society, Perkin Transactions 2
Дата:
1982
Аннотация:
Reduction of tris-(4-methoxyphenyl)methyl chloride (2) by refluxing methanol to tris-(4-methoxyphenyl)methane (3) is, as shown by <sup>2</sup>H labelling, accompanied by exchange of methoxy-groups between solvent and substrate. This exchange reaction appears to be the first recognized example of an S N2-Ar reaction of a triarylcarbenium ion and involves the intermediacy of the para-adduct (9a) which implies that in the course of the reduction of triarylcarbenium ions by n-nucleophiles, formation of the related type (1)ortho-adducts is possible as required by the Olahâ Svoboda mechanism.
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