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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions of 3,4,5-Trimethylbiphenyl and 2,3,4-Trimethylbiphenyl With Nitrogen Dioxide

MP Hartshorn, MC Judd, RJ Martyn, WT Robinson, GJ Wright and RW Vannoort

Australian Journal of Chemistry 43(9) 1519 - 1532
Published: 1990

Abstract

Reaction of 3,4,5-trimethylbiphenyl (1) with nitrogen dioxide gives four mononitro compounds (3)-(6) and three dinitro compounds (7)-(9). Similar reaction of 2,3,4-trimethylbiphenyl (2) gives three nitroaromatic compounds (11)-(13), three nitrate esters (14)-(16), and two nitro dienones (17) and (18). Dinitro dienone (17) rearranges in solution to give the corresponding hydroxy nitro dienone (19). The differences between the two sets of products are discussed, and an addition-elimination mechanism is proposed for the mode of formation of the nitro dienones (17) and (18). X-Ray crystal structures are reported for compounds (4) and (19).

https://doi.org/10.1071/CH9901519

© CSIRO 1990

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