Nitropyrroles—II
1970; Elsevier BV; Volume: 26; Issue: 21 Linguagem: Inglês
10.1016/s0040-4020(01)93163-1
ISSN1464-5416
AutoresA. Roy Cooksey, Keith J. Morgan, D.P. Morrey,
Tópico(s)Chemical Reactions and Mechanisms
ResumoThe nitration of pyrrole has been investigated for a variety of reagents and over a wide temperature range. The reaction with nitric acid proceeds smoothly in the presence of acetic anhydride and both direct spectroscopic observation and indirect kinetic results are in accord with acetyl nitrate acting as the effective reagent. For nitration in acetic anhydride the formation of nitropyrroles yields the ratio of 2-nitro: 3-nitro of ca 4 over a wide temperature range. By using extended series of competitive nitrations in acetic anhydride at 0° the reactivities of the 2- and 3-positions of the pyrrole ring are estimated as 130,000 and 30,000 respectively (with respect to benzene = 1).
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