para-Formylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with tris(benzotriazol-1-yl)methane

Reaction of nitroarenes 1 with tris(benzotriazol-1-yl)methyl 2 anion afforded para-bis(benzotriazol-1-yl)methylated products 3 which, upon treatment with zinc bromide and hydrochloric acid, yielded the corresponding p-nitroarylaldehydes 4 in good yields. Reaction of nitroarenes with tris(benzotriazo...

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Published inTetrahedron letters Vol. 37; no. 3; pp. 347 - 350
Main Authors Katritzky, Alan R., Linghong, Xie
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
SYNTHETIC METHODS
ORGANIC-ANIONS
CARBANIONS
ALDEHYDES
SULFONES
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Summary:Reaction of nitroarenes 1 with tris(benzotriazol-1-yl)methyl 2 anion afforded para-bis(benzotriazol-1-yl)methylated products 3 which, upon treatment with zinc bromide and hydrochloric acid, yielded the corresponding p-nitroarylaldehydes 4 in good yields. Reaction of nitroarenes with tris(benzotriazol-1-yl)methyl anion followed by treatment with zinc bromide and hydrochloric acid yielded the corresponding p-nitroarylaldehydes in good to excellent yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)02169-8