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Synthesis 2002(17): 2527-2531
DOI: 10.1055/s-2002-35619
PAPER
© Georg Thieme Verlag Stuttgart · New York

Studies on Phosphoroheterocycle Chemistry III: An Unusual Way to 1,3,2-Thiazaphospholidine-4-thione 2-Sulfide Derivatives

ShengLou Deng*a, RuYu Chenb
a School of Chemical Engineering, Tianjin University, Tianjin 300072, P. R. China
e-Mail: shengloudeng@hotmail.com;
b Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
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Publikationsverlauf

Received 24 June 2002
Publikationsdatum:
20. November 2002 (online)

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Abstract

An unusual but efficient method for the synthesis of phosphoroheterocycles, 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives, by the reaction of Lawesson’s reagent with a variety of α-hydroxy nitriles has been developed. The possible mechanism of the reaction is proposed to involve thiation of hydroxy group in a first step, sequential addition of P-SH to the nitrile and rearrangement resulting in the title phosphoroheterocycles. The preliminary bioassays show that these heterocyclic compounds have herbicidal properties.

Key words

Lawesson’s reagent - α-hydroxynitriles - 1,3,2-thiazaphospholidine-4-thione 2-sulfide - herbicidal activity