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Strukturvariationen durch Reaktionen der Thiocarbonylgruppe

Authors :
Wolfgang Hanefeld
Stephan Wurtz
Source :
Journal für praktische Chemie. 342:554-562
Publication Year :
2000
Publisher :
Wiley, 2000.

Abstract

Structural Variations by Reactions of the Thiocarbonyl GroupThe 2,3-dihydrothiazol-2-thiones 1a—c have been methylated to the 2-methylsulfanylthiazolium iodides 2a—c, which could be reacted with double activated CH-acidic compounds like 4-nitrophenylacetonitrile (3) to yield 5 and 6a,b, with malonic acid derivatives 7a—c to yield the push pull substituted ketene-S,N-acetales 8a—c or with 3-aminorhoda-nine derivatives to yield 12a,b. Vinylogous CH-acidic compounds like 9a—d reacted with 2b to the push-pull substituted butadienes 10a—d. With p-phenethidine 2b formed depending on the reaction conditions either the rare structure of an ortho-dithiocarbonic diester diamide (14) or the isothiourea 15. With hydrazino compounds, 16a—c with hydrazono partial structure resulted. Efforts to acylate the unsubstituted nitrogen of 17 with carbonic acid ester derivatives always yielded the S-acylated products 18 and 20a,b.

Details

ISSN :
15213897 and 14369966
Volume :
342
Database :
OpenAIRE
Journal :
Journal für praktische Chemie
Accession number :
edsair.doi...........b548e395085bb55de0d3bcb0245c49ae
Full Text :
https://doi.org/10.1002/1521-3897(200006)342:6<554::aid-prac554>3.0.co;2-6