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Synthesis and addition reactions of 1,3-Thiazole-5(4H)-thione Oxides


Shi, Junxing; Tromm, Peter; Heimgartner, Heinz (1994). Synthesis and addition reactions of 1,3-Thiazole-5(4H)-thione Oxides. Helvetica Chimica Acta, 77:2133-2141.

Abstract

1,3-Thiazole-5(4H)-thione oxides 2 were prepared by oxidation of the corresponding 1,3-thiazole-5(4H)-thiones 1 with m-chloroperbenzoic acid (Table 1). Addition reactions of 2 with organolithium and Grignard reagents yielded 4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-myelthyl sulfoxides of type 4 via thiophilic attack (Table 2). Whereas the reaction with the organolithium compounds proceeded with fair-to-excellent yields, the Grignard reagents reacted only very sluggishly.The sulfides 4 could also be prepared via oxidation of 4,5-dihydro-4,4-dimethyl-5-(methyIthio)-1,3-thiazoIes of type 3 with m-chloroperbenzoic acid, together with the corresponding sulfones 5 (Scheme I ) .

Abstract

1,3-Thiazole-5(4H)-thione oxides 2 were prepared by oxidation of the corresponding 1,3-thiazole-5(4H)-thiones 1 with m-chloroperbenzoic acid (Table 1). Addition reactions of 2 with organolithium and Grignard reagents yielded 4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-myelthyl sulfoxides of type 4 via thiophilic attack (Table 2). Whereas the reaction with the organolithium compounds proceeded with fair-to-excellent yields, the Grignard reagents reacted only very sluggishly.The sulfides 4 could also be prepared via oxidation of 4,5-dihydro-4,4-dimethyl-5-(methyIthio)-1,3-thiazoIes of type 3 with m-chloroperbenzoic acid, together with the corresponding sulfones 5 (Scheme I ) .

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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:1994
Deposited On:17 Dec 2013 11:57
Last Modified:08 Dec 2017 01:07
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19940770806

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