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Reactions of (1,3,3-Trichloro-2,2,4,4-tetramethylcyclobutyl)sulfenyl Chloride with Some S- and O-Nucleophiles


Woznicka, M; Mloston, G; Heimgartner, H (2009). Reactions of (1,3,3-Trichloro-2,2,4,4-tetramethylcyclobutyl)sulfenyl Chloride with Some S- and O-Nucleophiles. Phosphorus, Sulfur, and Silicon, 184(5):1314-1322.

Abstract

The sterically crowded 3,3-trichloro-2,2,4,4-tetramethylcyclobutanethione (2c) easily reacts with phosphorus pentachloride in CCl4 yielding the relatively stable (1,3,3-trichloro-2,2,4,4-tetramethylcyclobutyl)sulfenyl chloride (3c). The reactions of 3c with benzylsulfane (4) and thiocamphor (5) occur with elimination of HCl leading to the unsymmetrical disulfanes 6 and 9. In the case of the sulfenates 10 and 12, which are formed as intermediates in the reactions of 3c with propargyl and allyl alcohol, respectively, the subsequent [2,3]-sigmatropic rearrangement yields the corresponding sulfoxides 11 and 13.

Abstract

The sterically crowded 3,3-trichloro-2,2,4,4-tetramethylcyclobutanethione (2c) easily reacts with phosphorus pentachloride in CCl4 yielding the relatively stable (1,3,3-trichloro-2,2,4,4-tetramethylcyclobutyl)sulfenyl chloride (3c). The reactions of 3c with benzylsulfane (4) and thiocamphor (5) occur with elimination of HCl leading to the unsymmetrical disulfanes 6 and 9. In the case of the sulfenates 10 and 12, which are formed as intermediates in the reactions of 3c with propargyl and allyl alcohol, respectively, the subsequent [2,3]-sigmatropic rearrangement yields the corresponding sulfoxides 11 and 13.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:May 2009
Deposited On:25 Nov 2009 05:39
Last Modified:18 Apr 2018 11:40
Publisher:Taylor & Francis
ISSN:1026-7719
Funders:University of Lodz, F. Hoffmann-La roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1080/10426500902856412
Official URL:http://www.informaworld.com/smpp/content~db=all~content=a910780798~tab=citation

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