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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 14
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Original Articles

Novel Iodine Reagent System for Regioselective Cleavage of Epoxides to Alcohols

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Pages 2108-2112 | Received 27 Apr 2009, Published online: 17 Jun 2010
 

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.

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.[ Citation 11 , Citation 12 ]

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