The reduction of triarylcarbenium ions by alcohols: Simple hydride transfer or concerted breakdown of ortho-adducts?

Péter Huszthy, Károly Lempert, Gyula Simig, József Tamás

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Reduction of tris-(4-methoxyphenyl)methyl chloride (2) by refluxing methanol to tris-(4-methoxyphenyl)methane (3) is, as shown by 2H labelling, accompanied by exchange of methoxy-groups between solvent and substrate. This exchange reaction appears to be the first recognized example of an SN2-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 Olah-Svoboda mechanism.

Original languageEnglish
Pages (from-to)1671-1674
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number12
DOIs
Publication statusPublished - Jan 1 1982

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'The reduction of triarylcarbenium ions by alcohols: Simple hydride transfer or concerted breakdown of ortho-adducts?'. Together they form a unique fingerprint.

  • Cite this