METALATION OF TOLUENE . QUESTION OF KINETIC VS THERMODYNAMIC CONTROL
METALATION OF TOLUENE . QUESTION OF KINETIC VS THERMODYNAMIC CONTROL
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DOI：
10.1021/ja00970a012
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发表时间：
1966-01-01
影响因子：
15
通讯作者：
BROADDUS, CD
中科院分区：
文献类型：
--
作者：
BROADDUS, CD
正丁基钠对甲苯的金属化反应在短时间内可生成苄基钠和少量的环取代异构体。对甲苯钠对反应条件的稳定性研究表明，重排生成苄基钠的反应比较缓慢。在相同的反应条件下，甲苯与正丁基钾的金属化反应只生成苄基钾，这一点通过碳键化反应得到证实。这些结果进行了比较，金属化的烯烃，α-烯烃，和异丙苯与烷基钠和钾化合物。
Metalation of toluene by «-butylsodium has been shown toproduce benzylsodium, as well as minor amounts of ring-substituted isomers, after short reaction periods. Studies on the stability of p-sodiotolueneto the reaction conditions indicate that rearrangement to benzylsodium is comparatively slow. Metalation of toluene by n-butylpotassium under the same reaction conditions gave exclusively benzylpotassium, as evidenced by car-bonation. These results are compared to the metalation of a olefins, ethylbenzene, and cumene with alkylsodium and-potassium compounds.