Generation and Trapping of Phosphorus Stabilized 4,5-Ethylenedithio-1,3-dithiol-2-ide Carbanions: Synthesis of Ethylenedithio-1,3-dithiafulvalenes

Adrian J. Moore; Martin R. Bryce

doi:10.1055/s-1991-26370

Synthesis 1991; 1991(1): 26-28
DOI: 10.1055/s-1991-26370

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Generation and Trapping of Phosphorus Stabilized 4,5-Ethylenedithio-1,3-dithiol-2-ide Carbanions: Synthesis of Ethylenedithio-1,3-dithiafulvalenes

Adrian J. Moore^* , Martin R. Bryce

^*Department of Chemistry, University of Durham, Durham, DH1 3LE, England

Abstract

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2-Dimethoxyphosphoryl-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]-2-dithiin (8) and 2-triphenylphosphonio-5,6-dihydro-1,3-dithiolo-[4,5-b][1,4]dithiin tetrafluoroborate (9) have been obtained in four steps from 4,5-ethylenedithio-1,3-dithiole-2-thione (4) (ca. 75% overall yield). Deprotonation of (8) and (9) yields the corresponding carbanion (10) and ylide (11) which have been trapped in good yield with glyoxal, cyclopentanone and anthraquinone to afford ethylenedithio-1,3-dithiafulvalenes.

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