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Issue 19, 2010
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5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

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Abstract

5,5′-Dimethyl-3,3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated by filtration and recycled to its azoisoxazole by oxidation.

Graphical abstract: 5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

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Supplementary files

Article information


Submitted
17 Mar 2010
Accepted
17 Jun 2010
First published
16 Aug 2010

Org. Biomol. Chem., 2010,8, 4436-4443
Article type
Paper

5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

N. Iranpoor, H. Firouzabadi and D. Khalili, Org. Biomol. Chem., 2010, 8, 4436
DOI: 10.1039/C004357E

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