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The Course of the Willgerodt‐Kindler Reaction of Alkyl Aryl Ketones
Author(s) -
Asinger F.,
Schäfer Wolfgang,
Halcour K.,
Saus A.,
Triem H.
Publication year - 1964
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196400191
Subject(s) - geminal , chemistry , alkyl , flue gas desulfurization , aryl , organic chemistry , sulfur , medicinal chemistry
Ketones react with sulfur and NH 3 or amines at room temperature to produce Δ 3 ‐thiazolines, 5‐alkylidene‐Δ 3 ‐thiazolines, Δ 3 ‐imidazoline‐5‐thiones, hexathiacycloheptane derivatives, α,α′‐dioxodisulfides, bis‐(1‐aralk‐1‐yl) disulfides, or thiocarboxamides, depending on the coreactant and on the reaction conditions. It was recognized that the formation of all of these numerous types of compounds can be explained basically by primary thiolations and geminal dithiolations, which in conjunction with their reverse reaction (desulfurization) and the assumption of a thioreductone equilibrium permit a new interpretation of the course of the Willgerodt‐Kindler reaction of alkyl aryl ketones.