Pyrrole chemistry. VII. Syntheses and reactions of some N-substituted pyrroles

Abstract

In nitration, bromination, and formylation reactions 1-benzylpyrrole showed a greatly increased proportion of 3-substitution over both pyrrole and 1-methylpyrrole. The products of these reactions have been identified and interrelated. A number of attempts at hydrogenolysis under increasingly vigorous conditions failed to remove the benzyl group from methyl 1-benzyl-3-pyrrolecarboxylate. An attempt to use the 2,4-dinitrobenzenesulfenyl group to block the pyrrole nitrogen failed when the group entered the 2-position instead.