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The chemistry of cycloheptatriene Part VI: Interaction of 2,6-dimethylphenol and tropylium salts

✍ Scribed by R. van Helden; A. P. ter Borg; A. F. Bickel

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
248 KB
Volume
81
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The interaction of 2,6‐dimethylphenol and tropylium salts has been investigated. When the reaction is conducted in acetic acid solution cycloheptatriene and (4‐hydroxy‐3,5‐dimethylphenyl)tropylium salts (III) are formed. The yield of the latter depends on the anion present; it increases in the order: ClO~4~^−^ < BF~4~^−^ < Cl^−^ < CH~3~COO^−^. This reaction proceeds in two steps, viz. the primary formation of 2,6‐dimethyl‐4‐tropylphenol (IV) which then, by hydride ion transfer to tropylium ion, yields III. Isolation of the intermediate phenol was possible by the use of the heterogeneous system acetic acid ‐ water/hexane; upon reaction with tropylium salts it gave III.

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