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Intramolecular cyclization of ω-haloalkylsubstituted thiophosphorylacetonitriles: Synthesis and stereochemistry of 3-cyano-2-oxo-1,2-thiaphosphacyclanes

✍ Scribed by Irene L. Odinets; Natalya M. Vinogradova; Konstantin A. Lyssenko; Michail Yu. Antipin; Pavel V. Petrovskii; Tatyana A. Mastryukova

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
295 KB
Volume
13
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Intramolecular S‐alkylation in a series of ω‐haloalkyl‐substituted thiophosphorylacetonitriles 5–7 presents an effective synthetic route to the hitherto unknown 3‐cyano‐2‐oxo‐1,2‐thiaphospholanes 14 and thiaphosphinanes 15. The compounds were obtained as a mixture of cis‐ and trans‐isomers that were resolved to individual stereoisomers in most cases. For some of them, X‐ray diffraction analysis has been performed. It was shown that ^31^P NMR spectroscopy can be used to assign the stereochemistry of 3‐cyano‐2‐oxo‐1,2‐thiaphosphacyclanes. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:1–21, 2002; DOI 10.1002/hc.1101

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