Die Addition von 1-Lithio-1-(phenylthio)alkanen an 2-(N-Methylanilino)acrylnitril: Ein einfacher Weg zu 3-(Phenylthio)ketonen und 2-Enonen

Hubertus Ahlbrecht; Marcellinus Ibe

doi:10.1055/s-1988-27514

Synthesis 1988; 1988(3): 210-214
DOI: 10.1055/s-1988-27514

paper

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Die Addition von 1-Lithio-1-(phenylthio)alkanen an 2-(N-Methylanilino)acrylnitril: Ein einfacher Weg zu 3-(Phenylthio)ketonen und 2-Enonen

Hubertus Ahlbrecht^* , Marcellinus Ibe

^*Fachbereich Chemie der Universität Gießen, Institut für Organische Chemie, Heinrich-Buff-Ring 58, D-6300 Gießen, Federal Republic of Germany

Abstract

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The Addition of 1-Lithio-1-(phenylthio)alkanes to 2-(N-Methylanilino)-acrylonitrile: An Easy Access to 3-(Phenylthio)ketones and 2-Enones A simple and versatile strategy for the synthesis of the title compounds is described. The key-step consists in the addition of 1-lithio-1-(phenylthio)alkanes to 2-(N-methylanilino)acrylonitrile, the nucleophilic phenylthioalkylation of an enol-cation equivalent. Alkylation of the adducts and hydrolysis give 3-(phenylthio)ketones, which can be isolated, or without further purification can be transformed into 2-enones via the wellknown oxidation-elimination procedure. These reactions are possible with allylic derivatives too, therefore the homologous vinylic compounds can be prepared by the same way. Pyrolysis of the 1-lithioaminonitriles formed within the first step gives aminonitriles of cyclopropanones via cyclization.

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