Chemistry of Heterocyclic Compounds p. 518 - 524 (1983)
Update date:2022-09-26
Topics:
Koikov, L. N.
Terent'ev, P. B.
Gloriozov, I. P.
Torocheshnikov, V. N.
Baidin, V. N.
Bundel', Yu. G.
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.
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