1. The reactions of several types of organic sulfur compounds with chlorine and water, in acetic acid as a medium, have been studied.
Organic sulfides and mercaptans form addition compounds with anhydrous aluminum chloride in which there is presumably a dative bond between the sulfur and the aluminum atoms, i.e., R:S:R. A1CLIt might be supposed that one effect of the addendum would be to weaken the carbon-sulfur linkage and permit reactions which involve the breaking of this bond to occur. A search of the literature, and our own experiments indicate, however, that, under mild conditions, at room temperature, this is not generally the case. Aryl sulfides, such as diphenyl sulfide, form one-to-one addition complexes with aluminum chloride which remain unchanged in benzene, even in the presence of a substantial excess of aluminum chloride.1 This is also true of primary alkyl sulfides. Normal primary amyl sulfide was recovered unchanged after heating for two hours at 80°in benzene with more than one equivalent of aluminum chloride. Ethyl mercaptan, and n-amyl mercaptan showed little activity at room temperature in similar experiments. At the boiling point of benzene some hydrogen sulfide was evolved, but little or no alkylation of the benzene took place.It is generally observed that in molecules of the type A-CH2-B, the bond between CH2 and A or B is most easily broken when both A and B are negative in nature. It was thought, therefore, that if A, in A-CH2-S-B, Aids were such a negative atom or group, the activity of the complex would be enhanced. This idea was tested using the easily available and suitable compounds: benzyl mercaptan, benzyl sulfide, and s-trithiane. It was found that all three were quite active at room temperature when in contact with benzene and aluminum chloride.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.