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A new approach to α-(trifluoromethyl)benzyl substituted oxaziridines


Obijalska, Emilia; Mloston, Grzegorz; Utecht, Greta; Heimgartner, Heinz (2013). A new approach to α-(trifluoromethyl)benzyl substituted oxaziridines. Journal of Fluorine Chemistry, 151:7-11.

Abstract

The synthesis of N-substituted oxaziridines bearing an alpha-(trifluoromethyl)benzyl substituent at C(3) was achieved by m-CPBA oxidation of the corresponding 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols and their trimethylsilyl protected derivatives, respectively. In all cases, mixtures of diastereoisomers were formed. The prepared oxaziridine derivatives were shown to be able to oxidize thioanisole to thioanisole S-oxide in the presence of methanesulfonic acid.

Abstract

The synthesis of N-substituted oxaziridines bearing an alpha-(trifluoromethyl)benzyl substituent at C(3) was achieved by m-CPBA oxidation of the corresponding 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols and their trimethylsilyl protected derivatives, respectively. In all cases, mixtures of diastereoisomers were formed. The prepared oxaziridine derivatives were shown to be able to oxidize thioanisole to thioanisole S-oxide in the presence of methanesulfonic acid.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2013
Deposited On:29 Apr 2013 12:31
Last Modified:05 Apr 2016 16:46
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Centre (Poland) (Grant ‘SONATA’ # DEC-2011/03/D/ST5/05231)
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2013.03.018

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