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

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 pri...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-10, Vol.8 (19), p.4436-4443
Main Authors: Iranpoor, Nasser, Firouzabadi, Habib, Khalili, Dariush
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c004357e