Original reactions of α,α-dithio aryl alkanes with butyllithiums

A. Krief, B. Kenda, P. Barbeaux

Research output: Contribution to journalArticle

Abstract

Thioacetals derived from aromatic ketones react with butyllithiums already at -78°C and produce via a reductive process the corresponding α-thiobenzyllithiums in high yields. The same reaction also takes place selectively, under suitable conditions, with the thioacetals derived from benzaldehyde on which a competing metallation reaction is also possible. These observations clearly show that the thioacetal functionality is not a suitable protecting group against alkyllithiums for aromatic carbonyl compounds.
Original languageEnglish
Pages (from-to)2509-2512
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number22
DOIs
Publication statusPublished - 1 Jan 1991

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Carbonyl compounds
Alkanes
Ketones
benzaldehyde

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Krief, A. ; Kenda, B. ; Barbeaux, P. / Original reactions of α,α-dithio aryl alkanes with butyllithiums. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 22. pp. 2509-2512.
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Original reactions of α,α-dithio aryl alkanes with butyllithiums. / Krief, A.; Kenda, B.; Barbeaux, P.

In: Tetrahedron Letters, Vol. 32, No. 22, 01.01.1991, p. 2509-2512.

Research output: Contribution to journalArticle

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