Boron trifluoride hydrate-catalyzed competitive benzylation of benzene and toluene with benzyl and substituted benzyl chlorides.
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概要
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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 <I>k</I><SUB>T</SUB>/<I>k</I><SUB>B</SUB> 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 <I>k</I><SUB>T</SUB>/<I>k</I><SUB>B</SUB> 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.
- 公益社団法人 日本化学会の論文
著者
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NAKANE Ryohei
The Institute of Physical and Chemical Research
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Takematsu Akiko
The Institute of Physical and Chemical Research
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Sugita Kyoko
The Institute of Physical and Chemical Research
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