Novel Iodine Reagent System for Regioselective Cleavage of Epoxides to Alcohols

Abstract

Epoxides are converted regioselectively to corresponding higher substituted alcohols with greater yields using diphosphorus tetraiodide (P₂I₄) as a reducing agent and a catalytic amount of tetraethylammonium bromide at room temperature.

Keywords:

• Alcohols
• diphosphorus tetraiodide
• epoxides
• reduction
• tetraethylammonium bromide

ACKNOWLEDGMENT

V. N. T. and R. A. R. gratefully acknowledge the University Grants Commission, India, for financial support.

Notes

^a Typically, P₂I₄ (0.01 mol) reacted with epoxide (0.01 mol) in dichloromethane (50 ml, 1–3% moisture) in the presence of a catalytic amount of TEAB at room temperature.

^b Starting compounds were prepared by standard literature procedures.

^c Isolated yields after column chromatography and structure confirmed by comparison of IR and ¹H NMR with those of authentic materials.

^d Optical purity was confirmed by chiral HPLC and optical rotation matches with literature values.^{[ 11 , 12 ]}