Journal
TETRAHEDRON LETTERS
Volume 50, Issue 20, Pages 2347-2352Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.02.224
Keywords
Iodine; Catalyst; Esterification; Solvent-free
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The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol: high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry. (C) 2009 Elsevier Ltd. All rights reserved.
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