Issue 9, 1994
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereospecific formation of 2-[(E)-alk-1′-enyl]benzoic acids in an unusual reaction of thiophthalides with aldehydes

Dipakranjan Mal,   Gita Majumdar  and  Ranjan Pal  

Abstract

The reaction of thiophthalides 1 with aldehydes 3 in the presence of lithium tert-butoxide at –60 to 25 °C results in the stereospecific formation of only trans 2-(alk-1′-enyl)benzoic acids 4 in fairly good yields in one-pot operations. This reaction is proposed to proceed via episulfide formation followed by sulfur extrusion, and corroborated by an unprecedented reaction of phthalide with thiobenzophenone giving the acid 11a under similar conditions.

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Article information

DOI
https://doi.org/10.1039/P19940001115
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 1115-1116

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Stereospecific formation of 2-[(E)-alk-1′-enyl]benzoic acids in an unusual reaction of thiophthalides with aldehydes

D. Mal, G. Majumdar and R. Pal, J. Chem. Soc., Perkin Trans. 1, 1994, 1115 DOI: 10.1039/P19940001115

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