Organic Letters 2005-02-03

Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O) with alcohols in the presence of magnesium perchlorate. A new and general route to t-butyl ethers.

Giuseppe Bartoli, Marcella Bosco, Manuela Locatelli, Enrico Marcantoni, Paolo Melchiorre, Letizia Sambri

Index: Org. Lett. 7(3) , 427-30, (2005)

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Abstract

[reaction: see text] A new mild method for protecting alcohols as t-butyl ethers is reported. The reaction proceeds with Mg(ClO4)2 and Boc2O and shows general applicability. The deprotection of t-butyl ethers has also been revisited. Preliminary results indicate the CeCl3 x 7H2O/NaI system is a very suitable catalyst for their removal.