Fluorinated Ketene Dithioacetals;1. Preparation and Application to the Synthesis of α-Trifluoromethylthiocarboxylic S-Esters and Aldehyde Derivatives

Murielle Muzard; Charles Portella

doi:10.1055/s-1992-26280

Synthesis 1992; 1992(10): 965-968
DOI: 10.1055/s-1992-26280

paper

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Fluorinated Ketene Dithioacetals;1. Preparation and Application to the Synthesis of α-Trifluoromethylthiocarboxylic S-Esters and Aldehyde Derivatives

Murielle Muzard^* , Charles Portella

^*Laboratoire des Réarrangements Thermiques et Photochimiques (associé au CNRS), Faculté des Sciences, B. P. 347, F-51062 Reims, France

Abstract

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α-Trifluoromethylketene dithioacetals 3 were synthesized by Peterson reaction from trifluoromethyl ketones 1 and trimethylsilyl dithioacetals 2. Acid hydrolysis and reduction yielded α-trifluoromethylthiocarboxylic S-esters 4 and α-trifluoromethyl dithioacetals 5, respectively. Transacetalisation of the latter with ethanol gave the corresponding diethyl acetal. New procedures were developed to effect reduction and transacetalisation.

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