Hitomi Suzuki, K. Nakamura, M. Takeshima
Aug 1, 1971
Citations
0
Influential Citations
11
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Products obtained by the nitration of three isomeric dichloro and dibromotetramethylbenzenes with fuming nitric acid have been investigated. 3,6-Dihalo-1,2,4,5-tetramethylbenzene (dihalodurene) gave mainly 3,6-dihalo-2,4,5-trimethylbenzyl nitrate or 1,2-bis(nitrooxymethyl)-3,6-dihalo-4,5-dimethylbenzene, depending on the reaction temperature and the amount of nitrating agent. 4,6-Dihalo-1,2,3,5-tetramethylbenzene (dihaloisodurene) yielded a mixture of 3,5-dihalo-2,4,6-trimethylbenzyl nitrate and 2,6-dihalo-3,4,5-trimethylbenzyl nitrate, the latter in somewhat greater amount. 5,6-Dihalo-1,2,3,4-tetramethylbenzene (dihaloprehnitene) gave 5,6-dihalo-2,3,4-trimethylbenzyl nitrate as the sole nitrooxylation product. The reaction affords a new convenient route to precursors of various polysubstituted benzylic compounds hitherto not easily obtained by ordinary methods. Physical properties of some dihalotrimethylbenzylic compounds (chloride, nitrate, acetate, alcohol, and bisbenzyl ether) have been recorded.