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Transformations of 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptyl glycidyl ether upon the action of nucleophiles and reducing agents

Transformations of 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptyl glycidyl ether upon the action of... Selective substitution of the iodine atom for hydrogen in 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptyl glycidyl ether has been performed upon the action of Bu3SnH/Bz2O2, which led to the corresponding deiodination product in 82% yield. The epoxide ring opening in the title substrate was observed in its reaction with methanol and acetone in the presence of a Lewis acid, as well as upon the action of thiourea, morpholine, and sodium azide. In the last two cases, the formation of secondary alcohols is accompanied by dehydroiodination. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Chemical Bulletin Springer Journals

Transformations of 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptyl glycidyl ether upon the action of nucleophiles and reducing agents

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References (13)

Publisher
Springer Journals
Copyright
Copyright © 2009 by Springer Science+Business Media, Inc.
Subject
Chemistry; Inorganic Chemistry ; Organic Chemistry; Chemistry/Food Science, general
ISSN
1066-5285
eISSN
1573-9171
DOI
10.1007/s11172-009-0158-4
Publisher site
See Article on Publisher Site

Abstract

Selective substitution of the iodine atom for hydrogen in 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodoheptyl glycidyl ether has been performed upon the action of Bu3SnH/Bz2O2, which led to the corresponding deiodination product in 82% yield. The epoxide ring opening in the title substrate was observed in its reaction with methanol and acetone in the presence of a Lewis acid, as well as upon the action of thiourea, morpholine, and sodium azide. In the last two cases, the formation of secondary alcohols is accompanied by dehydroiodination.

Journal

Russian Chemical BulletinSpringer Journals

Published: Apr 27, 2010

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