Boron Trifluoride Hydrate-catalyzed Competitive Benzylation of Benzene and Toluene with Benzyl and Substituted Benzyl Chlorides

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公開日
1978-07-01
権利情報
  • https://academic.oup.com/pages/standard-publication-reuse-rights
DOI
  • 10.1246/bcsj.51.2082
公開者
Oxford University Press (OUP)

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<jats:title>Abstract</jats:title> <jats:p>The competitive benzylation of benzene and toluene catalyzed by boron trifluoride hydrate was carried out with benzyl, chlorobenzyl, alkylbenzyl, and alkoxybenzyl chlorides in boron trifluoride hydrate and hexane solutions. The relative rates of toluene to benzene were smaller than 1 in the benzylation with benzyl and chlorobenzyl chlorides, while they were larger than 1 with alkylbenzyl and alkoxybenzyl chlorides. Competitive benzylation catalyzed by boron trifluoride was also carried out in a nitromethane solution. The relative rates were reduced by from several to ten times in the former solutions as compared to the latter solution; the kT/kB value became smaller than 1 when the electrophile was such a very strongly electron-deficient reagent as the benzyl or chlorobenzyl cation. On the other hand, the kT/kB value was still larger than 1 when the electrophilicity was lower, as in the alkylbenzyl or alkoxybenzyl cation. The isomer distribution was insensitive to the nature of the solvents. The formation of the meta isomer was always only a small percentage. These results substantiate our previous conclusions obtained in the ethylation and isopropylation catalyzed by boron trifluoride hydrate.</jats:p>

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