Nucleophilic solvent participation in the solvolysis of 4-methoxybenzyl bromide and chloride

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题名:	Nucleophilic solvent participation in the solvolysis of 4-methoxybenzyl bromide and chloride
作者:	Liu,KT;Duann,YF;Hou,SJ
贡献者:	中央大學
关键词:	BENZYLIC SOLVOLYSES;SATURATED CARBON;SODIUM AZIDE;SCALE;ION;SUBSTITUTION;SECONDARY;REACTIVITIES;INTERVENTION;DERIVATIVES
日期:	1998
上传时间:	2010-06-29 19:47:39 (UTC+8)
出版者:	化學研究所
摘要:	The solvolysis of 4-methoxybenzyl chloride (1) and bromide (3), and 1-(4-methoxyphenyl)ethyl chloride (4) in a variety of solvents were carried out. The observation of linear correlation using the dual-parameter Grunwald-Winstein equation, and the positive azide salt effect indicate significant nucleophilic solvent participation for 1 and 3, A smaller deviation of log k (in 100% 2,2,2-trifluoroethanol) for the bromide 3 than chloride 1 in the log k - Y-BnX plots reveals a lesser extent of nucleophilic participation and is also in harmony with the greater nucleofugality of the bromide ion. The use of a low k(Br)/k(Cl) ratio as evidence for the presence of solvent participation is discussed. The observed alpha-deuterium kinetic isotope effect of 1.08 to 1.21 measured for 1 and 3 is inconsistent with the magnitude generally considered for a concerted mechanism.
關聯:	JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
显示于类别:	[化學研究所] 期刊論文

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