First General Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 12; pp. 4137 - 4141
Main Authors Katritzky, Alan R, Toader, Dorin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.06.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITROARENES
TRIARYLMETHANES
Online AccessGet full text

Cover

More Information
Summary:A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel−Crafts reactions for the synthesis of triarylmethanes.
Bibliography:ark:/67375/TPS-9DCPMGD3-J
istex:D5F4A10A1C2851E3ED9C6488AE35B16008D3D3D3
Abstract published in Advance ACS Abstracts, April 15, 1997.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9624197