Monatshefte fur Chemie, ( ISI ), Volume (135), Year (2004-9) , Pages (1101-1111)

Title : o-Phenylenediamine as a New Catalyst in the Highly Regioselective Conversion of Epoxides to Halohydrins with Elemental Halogens ( o-Phenylenediamine as a New Catalyst in the Highly Regioselective Conversion of Epoxides to Halohydrins with Elemental Halogens )

Authors: Hossein Eshghi , Sayyed Faramarz Tayyari , Esmaiel Sanchuli ,

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The regioselective ring opening of epoxides using elemental iodine and bromine in the presence of o-phenylenediamine as a new catalyst affords vicinal iodo alcohols and bromo alcohols in high yields. The major advantages of this method are versatility, high regioselectivity, a cheap and commercially available catalyst, mild and neutral reaction conditions, and short reaction times. Fourier transform Raman spectroscopy was used to study the reaction of iodine with o-phenylenediamine. The results indicate that the complex [(Diamine)I]þ  I5  is formed, and we suggest that the major nucleophile is the pentaiodide ion. This bulky nucleophile has a fundamental role in the high regioselectivity observed attacking the less sterically hindered epoxide carbon.

Keywords

Catalyst; Diamines; Epoxides; Halohydrin; FT Raman
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@article{paperid:1005814,
author = {Eshghi, Hossein and Tayyari, Sayyed Faramarz and Esmaiel Sanchuli},
title = {o-Phenylenediamine as a New Catalyst in the Highly Regioselective Conversion of Epoxides to Halohydrins with Elemental Halogens},
journal = {Monatshefte fur Chemie},
year = {2004},
volume = {135},
month = {September},
issn = {0026-9247},
pages = {1101--1111},
numpages = {10},
keywords = {Catalyst; Diamines; Epoxides; Halohydrin; FT Raman spectroscopy},
}

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%0 Journal Article
%T o-Phenylenediamine as a New Catalyst in the Highly Regioselective Conversion of Epoxides to Halohydrins with Elemental Halogens
%A Eshghi, Hossein
%A Tayyari, Sayyed Faramarz
%A Esmaiel Sanchuli
%J Monatshefte fur Chemie
%@ 0026-9247
%D 2004

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