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Syntheses and thermal transformations of N-alkyl thiazolidine sulfoxides

✍ Scribed by Stephen R Herchen

Book ID
104227039
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
208 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title compounds are prepared and their novel thermal chemistry studied for the first time. Aldehydes and thiazolidines can be generated thermally from these compounds. Mechanistic possibilities are discussed.

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## Abstract Stereospecific ring opening of the sulfoxides __cis__‐13 and __trans__‐14 in refluxing toluene gave the corre sponding sulfenic acids 9, 10 intermediates respectively. The sulfenic acid 9 dimerized to the thiolsulfinate 17 by dual function of the sulfenic acid as __S__‐nucleophile/__S__

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Thermal Rearrangement of 1,3-Thiazolidine Sulfoxides: Thiosulfinate and Thioaldehyde Intermediates. -As an extension of studies on the reactivity and synthetic uses of sulfoxides and sulfenic acids, the thermal rearrangement of title compound (I) is investigated. The formation of the products (II)-