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Updated: Jul 16, 2026

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Published on: February 7, 2019
Highly stereoselective chlorination of beta-substituted cyclic alcohols using PPh3-NCS: factors that control the
E A Jaseer1, Ajay B Naidu, Sreehari S Kumar
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu, 600 036, India.
Abstract:
A variety of trans-beta-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the beta-substituents, especially the electronegativity of the substituted atom.
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