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Synthesis 2017; 49(24): 5335-5338
DOI: 10.1055/s-0036-1589103
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© Georg Thieme Verlag Stuttgart · New York

A Practical Gram-Scale Synthesis of Acrylohydroxamic Acid

Bruce C. Hamper*
a   Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: hamperb@umsl.edu
,
Brendan T. Sullivan
a   Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: hamperb@umsl.edu
,
Nigam P. Rath
b   Center for Nanoscience, Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA
,
Christopher D. Spilling
a   Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA   Email: hamperb@umsl.edu
› Author AffiliationsThis work was supported by a contract from ALKYMOS, Inc. Funding for the ApexII diffractometer was provided by the National Science Foundation (MRI, CHE-0420497).
Further Information

Publication History

Received: 15 July 2017

Accepted after revision: 09 August 2017

Publication Date:
30 August 2017 (online)

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Abstract

Acrylohydroxamic acid, which is a useful monomer for the preparation of polymeric materials, has been prepared in a straightforward, two-step synthesis from readily available starting materials. The key steps are coupling of acrylic acid with O-tetrahydropyranylhydroxyl amine to provide protection of the hydroxylamine functionality, followed by acid cleavage of the protecting group.

Key words

hydroxamic acids - acrylohydroxamic acid - chelating agents - monomers - functionalized polymers - metal chelation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589103.
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