Volume 21, Issue 37
Preparative Organic Chemistry
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ChemInform Abstract: Alkylation of the 2,4,6-Triphenylthiopyran Anion.

J. S. KRISTENSEN

J. S. KRISTENSEN

Dep. Org. Chem., Univ. Aarhus, DK-8000 Aarhus C, Den.

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H. LUND

H. LUND

Dep. Org. Chem., Univ. Aarhus, DK-8000 Aarhus C, Den.

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First published: September 11, 1990

Abstract

The electrochemical reduction of the triphenylthiopyrylium cation (I) is investigated by cyclic voltammetry and preparative reduction in the presence of alkyl halides such as (II) to give the products (III) and (IV).

ChemInform Abstract

The electrochemical reduction of the triphenylthiopyrylium cation (I) is investigated by cyclic voltammetry and preparative reduction in the presence of alkyl halides such as (II) to give the products (III) and (IV). The rate-determining step in the coupling between the anion derived from (I) and the alkyl halide (II) is shown to be an electron transfer, followed by coupling of the thereby formed thiopyranyl and tert.-butyl radicals. Similarities in the corresponding reactions of the anions derived from 2H-thiopyran and dihydropyridine are discussed.

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