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The (silylethynyl)- and the (tolylethinyl)-hydrazines 1a and 1b react with aryl isocyanates 2a-e and arylsulfonyl isocyanates 2f,g to form the corresponding substituted 3-arylimino-(or arylsulfonylimino-) 1,1,2-trimethyl-5-oxopyrazolidinium-4-ides 3a-h. The silyl group in the 4-position can be replaced by a hydrogen atom (formation of 6a-e). Heating of 6d in toluene induced the unequivocal transformation of the betaine to an isomer, the spectrocopic data of which are in concordance with those of the 4-quinolone derivative 7. Aroyl isocyanates 8 react in a [4+2]cycloaddition with 1a to furnish the 1,3-oxazin-4-ones 9a and b. The stannylated ynehydrazine 1c adds the cumulenic system of an aryl isocyanate (2d) across the Csp-Sn single bond, and trimethylstannyl N-(p-chlorophenyl)-3-(trimethylhydrazmo)propiolimidate 10 is isolated. With two molecules of 2d the hydantoin derivative 11 is formed.
- Himbert, Gerhard,Gerulat, Oliver
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p. 1196 - 1204
(2007/10/03)
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- THIOCYANATO-, BROMO-, AND CHLOROARYLATION OF TRICHLOROETHYLENE
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By reactions of arenediazonium salts with trichloroethylene in aqueous acetone in the presence of alkali metal thiocyanates, bromides, or chlorides, catalyzed by Cu(II) or Fe(II) salts, we synthesized 1-thiocyanato(bromo, chloro)-1,2,2-trichloro-2-arylethanes.These were treated with alcoholic potassium hydroxide to give α,β,β-trichlorostyrenes.Trichloroethylene is less reactive in the anionarylation than vinylidene and vinyl chlorides.
- Grishchuk, B. D.,Kudrik, E. Ya.,Gorbovoi, P. M.,Garmider, V. L.,Ganushchak, N. I.
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p. 1164 - 1166
(2007/10/02)
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