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Org Biomol Chem. 2010 Oct 7;8(19):4436-43. doi: 10.1039/c004357e. Epub 2010 Aug 16.

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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  • 1Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran. iranpoor@susc.ac.ir

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.

PMID:
20714494
[PubMed]
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