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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 and Letizia Sambri

*Dipartimento di Chimica Organica "A. Mangini", v.le Risorgimento 4, I-40136 Bologna, Italy, Email: giuseppe.bartoliunibo.it

G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, P. Melchiorre, L. Sambri, Org. Lett., 2005, 7, 427-430.

DOI: 10.1021/ol047704o (free Supporting Information)


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Abstract

A mild reaction for the protection of alcohols as t-butyl ethers proceeds with Mg(ClO4)2 and Boc2O and shows general applicability. In addition, preliminary results indicate that the CeCl37H2O/NaI system is a very suitable catalyst for the deprotection of t-butyl ethers.

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Key Words

tert-Butyl Ethers


ID: J54-Y2005-190