Nitrations with Acetyl nitrate. I. The nature of the nitrating agent and the mechanism of reaction with simple alkenes

FG Bordwell, EW Garbisch Jr

Index: Bordwell,F.G.; Garbisch,E.W. Journal of the American Chemical Society, 1960 , vol. 82, p. 3588 - 3598

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Citation Number: 69

Abstract

Acetyl nitrate in acetic acid-acetic anhydride solution reacts within five minutes with cis-and trans-2-butenes, 2-methylpropene, 2-methyl-2-butene, cyclopentene, cyclohexene and 1- methylcyclohexene to give p-nitro acetates in 20-64y0 yields and p-nitroalkenes in 3-50'% yields. Under these conditions 1-butene, 3-methyl-l-butene, 2, 3, 3-trimethyl-l-butene, 2, 4, 4- trimethyl-2-pentene. 3-chloro-2-methyl-lpropene, 2-bromopropene and 2-acetoxypropene ...