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Synthesis 2013; 45(3): 326-329
DOI: 10.1055/s-0032-1317861
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Revised Preparation of (4-Acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate: Reagents for Stoichiometric Oxidations of Alcohols

Leon J. Tilley
a   Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: ltilley@stonehill.edu
,
James M. Bobbitt*
b   Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: james.bobbit@uconn.edu
,
Stephanie A. Murray
a   Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: ltilley@stonehill.edu
,
Casey E. Camire
a   Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: ltilley@stonehill.edu
b   Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: james.bobbit@uconn.edu
,
Nicholas A. Eddy
b   Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: james.bobbit@uconn.edu
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Further Information

Publication History

Received: 01 August 2012

Accepted after revision: 20 November 2012

Publication Date:
21 December 2012 (online)

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Abstract

Revised preparations of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and the corresponding oxoammonium salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxoammonium tetrafluoroborate are presented together with some of the important properties of these two oxidizing­ reagents.

Key words

oxidations - catalysis - green chemistry - alcohols - aldehydes - ketones