Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent

Michael W. Justik

doi:10.1016/j.tetlet.2007.02.129

Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent

Michael W. Justik

School of Science (Behrend)

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

Previous methods for the conversion of arylalkanones to alkyl 2-arylesters by oxidative rearrangement utilized reagents which either produced toxic metal salts or halogenated organics as by-products. In this report, 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI) is used to effect this useful transformation, where the reduced iodine reagent is water-soluble and readily recycled.

Original language	English (US)
Pages (from-to)	3003-3007
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2007.02.129
State	Published - Apr 23 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.02.129

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title = "Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent",

abstract = "Previous methods for the conversion of arylalkanones to alkyl 2-arylesters by oxidative rearrangement utilized reagents which either produced toxic metal salts or halogenated organics as by-products. In this report, 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI) is used to effect this useful transformation, where the reduced iodine reagent is water-soluble and readily recycled.",

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N1 - Funding Information: We thank Penn State Erie, The Behrend College for financial support through new faculty start-up funds. The Bruker Avance 400 MHz NMR Spectrometer used in this work was made possible by gifts from the Thomas Lord Charitable Trust and The Orris C. Hirtzel and Beatrice Dewey Hirtzel Memorial Foundation. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

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AB - Previous methods for the conversion of arylalkanones to alkyl 2-arylesters by oxidative rearrangement utilized reagents which either produced toxic metal salts or halogenated organics as by-products. In this report, 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI) is used to effect this useful transformation, where the reduced iodine reagent is water-soluble and readily recycled.

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Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent

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