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Paper | Special issue | Vol 40, No. 2, 1995, pp.743-752
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S62
Reactions of an o-Quinone Monoimide with Pyrroles

Harold W. Heine, Matthew G. LaPorte, Robert H. Overbaugh, and Elizabeth A. Williams

*Department of Chemistry, Bucknell University, Lewisburg, PA 17837, U.S.A.


The o-quinone monoimide (7) undergoes inverse electron demand Diels-Alder reactions with 1-benzenesulfonyl- and 1-carbomethoxypyrroles. The initial adduct (9), formed when 7 interacts with 1-carbomethoxypyrrole, underwent a further cycloaddition with 7 yielding a 2:1 adduct (10). Similar 2:1 adducts result when 7 reacts with 1-methyl-2-acetyl- and 1-methyl-2-carbomethoxypyrroles. Compound (7) reacts formally as an electrophile when it is admixed with 1-methyl- and 1-methyl-3-acetylpyrroles to give substituted pyrroles.