REACTIVITIES OF ISOMERIC (1-DIMETHYLAMINOVINYL)PYRIDINES. REACTION WITH SULFENE

Article abstract of DOI:10.1007/BF00514462

It is shown by means of quantum-chemical calculations (MINDO/3) and data from the 13C NMR and photoelectron (PE) spectra that a weak interaction between the enamine fragment and the heteroring, which deviates from its plane, exists in pyridyl enamines.The reaction of (1-dimethylaminovinyl)pyridines with sulfene leads to mixtures of 3-dimethylamino-3-pyridylthietane 1,1-dioxide (80percent) and the corresponding methylsulfonyl ketone, the yield of which decreases as the acceptor character of the aromatic ring increases (α-Py < γ-Py < β-Py < Ph).The structures of the enamines and the products of their reaction with sulfene were proved by IR, UV, and PMR spectroscopy, mass spectrometry, and the results of elementary analysis.