The nitration of styrenes by nitric acid in dichloromethane

Autor:	Richard J. Lewis, Roy B. Moodie
Rok vydání:	1997
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Nitrate Nitric acid Alkene Nitration Kinetics Organic chemistry Carbocation Medicinal chemistry Transition state Dichloromethane
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :563-568
ISSN:	1364-5471 0300-9580
DOI:	10.1039/a605782i
Popis:	Kinetics and products of reaction of 4-R-styrenes (R = Me, H, Cl, CF3, NO2) with nitric acid in dichloromethane are reported. Reaction occurs in the alkene group and aromatic nitration is insignificant. With increasingly electron-withdrawing substituents the reaction changes from one which is third order in nitric acid and gives rise to the 1-arylethyl nitrate, to one which is of higher order in nitric acid and gives rise to the 2-nitro-1-arylethyl nitrate (β-nitro-nitrate). Both reactions proceed through transition states with carbocation character, by initial β-addition of H+ and NO2+ respectively. The β-nitro-nitrate is formed in part also by a radical pathway, as are other minor products.
Databáze:	OpenAIRE
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