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Paper | Regular issue | Vol 48, No. 10, 1998, pp.2019-2034
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8241
Selective Thiophilic Addition of Alkyl- and Aryllithiums to Dithio Esters and a Sulfine in the Pyridine Series

Claude Lempereur, Nelly Plé, Alain Turck, Guy Quéguiner,* Florence Corbin, Carole Alayrac, and Patrick Metzner*

*Laboratoire de Chimie Moléculaire et Thio organique, UMR CNRS 6507, ISMRA-Université, 6 Boulevard du Maréchal Juin, 14050 Caen, France

Abstract

Reaction of two dithio esters and a new sulfine (S-thiocarbonyl oxide) with various aryl- and alkyllithiums at -78 °C afforded dithio acetals or their oxides, arising from a thiophilic addition. The intermediate carbanions can be trapped by alkyl halides or an aldehyde. This provides a new entry to pyridyl acyl anions, "Umpolung" synthons.