Issue 1, 1975

Selective nitration of aromatic substrates: reaction of nitrogen dioxide with arylthallium(III) compounds

Abstract

A method of selectively nitrating aromatic substrates is described in which nitrogen dioxide displaces a thallium(III) substituent electrophilically. High yields of the para-isomer were obtained from alkylbenzenes and a number of other substrates containing orthopara-directing groups. Similar specificity was observed with xylenes but the process proved only partially successful when applied to mesitylene where, it is postulated, steric interaction between the methyl groups and the bulky thallium substituent inhibits the reaction. Thermodynamic control leading to meta-isomers proved impossible, a low yield of nitroarenes being obtained, the bulk of which originates by direct attack of nitrogen dioxide on regenerated aromatic substrate. Compounds with side-chains which have been reported to direct the incoming thallium substituent to an ortho-site also failed to react and an explanation for this is offered.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 65-70

Selective nitration of aromatic substrates: reaction of nitrogen dioxide with arylthallium(III) compounds

B. Davies and C. B. Thomas, J. Chem. Soc., Perkin Trans. 1, 1975, 65 DOI: 10.1039/P19750000065

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements