Esters and Amides from Activated Alcohols using Manganese(IV) Dioxide: Tandem Oxidation Processes

Jonathan S. Foot; Hisashi Kanno; Gerard M. P. Giblin; Richard J. K. Taylor

doi:10.1055/s-2003-39163

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Synthesis 2003(7): 1055-1064
DOI: 10.1055/s-2003-39163

PAPER

Esters and Amides from Activated Alcohols using Manganese(IV) Dioxide: Tandem Oxidation Processes

Jonathan S. Foot^a, Hisashi Kanno^a, Gerard M. P. Giblin^b, Richard J. K. Taylor*^a
^a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
^b Department of Medicinal Chemistry, Neurology and GI CEDD, GlaxoSmithKline, The Frythe, Welwyn, Herts AL6 9AR, UK

Further Information

Publication History

Received 25 February 2003
Publication Date:
09 May 2003 (online)

Abstract
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Abstract

Manganese(IV) dioxide can be used in conjunction with sodium cyanide in THF-methanol or in methanol alone for the direct conversion of activated alcohols into methyl esters. Ethyl and isopropyl esters can also be prepared. Similarly, use of manganese(IV) dioxide and sodium cyanide in THF containing ammonia or primary amines can be used to convert alcohols into the corresponding amides. Several activated alcohols and one non-activated alcohol example are reported.

Key words

alcohols - amides - esters - oxidations - tandem reactions

References

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2,4-Dodecadien-1-ol purchased from Fluka, cat. no. 00554.