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Synthesis 2010(10): 1633-1638  
DOI: 10.1055/s-0029-1218712
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Noncatalytic Electrophilic Oxyalkylation of Anilines with 2-Trifluoroacetyl-1,3-benzothiazole

Pavel V. Khodakovskiya,b, Pavel K. Mykhailiuk*a,b, Dmitriy M. Volochnyuka, Andrey A. Tolmacheva,b
a Enamine Ltd., Alexandra Matrosova Street 23, Kiev 01103, Ukraine
b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, Kiev 01033, Ukraine
Fax: +38(44)2351273; e-Mail: Pashamk@gmx.de;
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Publication History

Received 18 February 2010
Publication Date:
24 March 2010 (online)

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Abstract

2-Trifluoroacetyl-1,3-benzothiazole reacts with anilines to form the corresponding trifluoromethyl-substituted alcohols. The reaction regioselectivity (ortho/para) was shown to depend strongly on the structure of the aniline. meta-Substituted anilines tend to form the corresponding ortho-substituted products, in contrary to the previous literature data.

Key words

anilines - Friedel-Crafts alkylation - ortho/para-substitution - trifluoromethyl alcohols - 1,3-benzothiazole

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