Unusual product from the nitration of 2,3,4-trimethylneopentylbenzene: 3-(2,3,4-trimethyl-5-nitrophenyl)-2-methyl-1-nitrobut-2-ene. Evidence for the heterolytic mechanism of side-chain substitution of arenes
Abstract
During nitration of 2,3,4-trimethylneopentylbenzene the neopentyl group isomerises giving the title nitro-olefin as one of the main products; the result strongly suggests the intervention of a carbonium ionic species in the side-chain substitution of arenes.