Tetrahedron Letters

Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions

M Jereb, D Vražič, M Zupan

Index: Jereb, Marjan; Vrazic, Dejan; Zupan, Marko Tetrahedron Letters, 2009 , vol. 50, # 20 p. 2347 - 2352

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Citation Number: 20

Abstract

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 ...