Cycloaddition of Bis[3,3-bis(diethylamino)thioacryloyl] Disulfide with Alkynic Dienophiles

Cycloaddition of Bis[3,3-bis(diethylamino)thioacryloyl] Disulfide with Alkynic Dienophiles

The reaction of bis[3,3-bis(diethylamino)thioacryloyl] disulfide (1) with dimethyl acetylenedicarboxylate gave dimethyl 4-diethylamino-2-thioxo-2H-thiopyran-5,6-dicarboxylate in 69% yield. Similarly, a series of alkynic dienophiles reacted with 1 to give the corresponding 2H-thiopyran-2-thione deriv...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 1996-07, Vol.69 (7), p.2091
Hauptverfasser: Akimoto, Keiichi, Masaki, Kazuto, Nakayama, Juzo
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creator Akimoto, Keiichi
Masaki, Kazuto
Nakayama, Juzo
description The reaction of bis[3,3-bis(diethylamino)thioacryloyl] disulfide (1) with dimethyl acetylenedicarboxylate gave dimethyl 4-diethylamino-2-thioxo-2H-thiopyran-5,6-dicarboxylate in 69% yield. Similarly, a series of alkynic dienophiles reacted with 1 to give the corresponding 2H-thiopyran-2-thione derivatives in modest-to-reasonable yields. A full experimental description of this 2H-thiopyran-2-thione formation is given and a mechanism involving [4+2]cycloaddition followed by homolytic cleavage of the S-S bond is presented.
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source Oxford University Press Journals All Titles (1996-Current)
title Cycloaddition of Bis[3,3-bis(diethylamino)thioacryloyl] Disulfide with Alkynic Dienophiles
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