Addition reactions of heterocycles. VII. Pyrrole andC-Acetyl-N-phenylnitrilimine

Autor: Nicolò Vivona, Gabriella Macaluso, Giuseppe Cusmano, Michele Ruccia
Rok vydání: 1978
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 15:1485-1488
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570150847
Popis: The addition reaction of C-acetyl-N-phenylnitrilimine to pyrrole has been investigated. The products obtained show that the reaction proceeds via two distinct pathways. The 1,3-addition reaction leads to the non-cyclic-adduct III, whereas the 1,3-cycloaddition reaction gives a mixture of regioisomeric Δ2-pyrroline IV and V, and Δ1 -pyrroline VI and VII mono-cycloadducts. These latter compounds cannot be isolated because they undergo a further 1,3-cycloaddition reaction leading to the N-substituted bis-adducts X and XI, and to the bis-adduets XII and XIII. The stereochemical assignment for X, XI, XII and XIII is provided by nmr data which suggest also that in X and XI the rotation around the exocyclic N-C bond is relatively slow on the instrument time scale.
Databáze: OpenAIRE
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