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1 Polish Journal of Chemistry

1 2000

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Reaction of - and -Halogenostyrenes with Arenediazonium Tetrafluoroborates and Potassium Thiocyanate

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Bila E. E. , Obushak M. D. , Ganushchak M. I.

Polish Journal of Chemistry

2000

tom Vol. 74, nr 11

1567-1567

Reaction between alfa- and beta-monohalogenostyrenes 1–4, arenediazonium tetrafluoroborates 5a–e and potassium thiocyanate under catalytic condition (Cu2+) proceeds unusually. It was shown that direction of these reactions depends on the halogen position and the solvent: alfa-substituted (H, Cl or SCN) stilbenes or products of thiocyanatoarylation have been obtained. beta-Chloro- 1 and beta-bromostyrenes 2 react with 5a–e and KSCN to form substituted trans-stilbenes 6a–e and Z-alfa-thiocyanatostilbenes 7a–e. beta-Chloro- 3 and beta-bromostyrenes 4 react with 5a–e and KSCN in acetone or acetone- water medium to form products 6a–e and 7a–e. The 4-nitrobenzenediazonium tetrafluoroborate (5e) gives of Z-alfa-chloro-4-nitrostilbene (9e) besides 6e and 7e. In acetone- water medium -chlorostyrene (3) gives also 1-chloro-1-thiocyanato-1-phenyl- -2-arylethanes 8a–e and moreover products 6a–e and 7a–e. The radical cation mechanism for these reactions has been discussed. It is postulated that the reaction takes place through the formation of radical cations [PhCH=CHHal]+. or [PhCHal=CH2]+. with further formation of phenylvinyl cations.