Volume 19, Issue 13
Isocyclic Compounds
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ChemInform Abstract: Allyl Sulfide Synthesis of Phenylthio Migration: Relationship Between Stereochemistry of Starting Materials and Regioselectivity of Double Bond Formation.

V. K. AGGARWAL

V. K. AGGARWAL

Univ. Chem. Lab., Cambridge Univ., Cambridge CB2 1EW, UK

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S. WARREN

S. WARREN

Univ. Chem. Lab., Cambridge Univ., Cambridge CB2 1EW, UK

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First published: March 29, 1988

Abstract

Reduction of the phenylthio ketone (I) affords the syn- and anti-phenylthio alcohols (II) and (III).

ChemInform Abstract

Reduction of the phenylthio ketone (I) affords the syn- and anti-phenylthio alcohols (II) and (III). Phenylthio migration of each isomer preferentially leads to one of the two regioisomeric allylic sulfides (IV) and (V). Other examples are given; the regioselectivities of double bond formation and the E/Z selectivities of the formed allylic sulfides are affected by the substituents.

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