Acylation of 2-methoxynaphthalene with acyl chlorides in the presence of a catalytic amount of Lewis acids
Acylation of 2-methoxynaphthalene with acyl chlorides in the presence of a catalytic amount of Lewis acids
复制标题
在催化量的路易斯酸存在下，2-甲氧基萘与酰氯的酰化
DOI：
10.1039/p19940001703
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发表时间：
1994
期刊：
影响因子：
--
通讯作者：
M. Nomura
中科院分区：
文献类型：
--
作者：
S. Pivsa‐Art;Kazumi Okuro;M. Miura;S. Murata;M. Nomura
在催化量的Lewis酸的作用下，2-甲氧基萘1与苯甲酰氯2a反应的区域化学受所用酸催化剂的特性以及反应温度的强烈影响。用InCl3、FeCl3、SnCl4或ZnCl2在160℃加热时，2-苯甲酰基-6-甲氧基萘4a与1-苯甲酰基-7-甲氧基萘5a一起选择性地生成，而在AlCl3、SbCl5或TiCl4的情况下，1-苯甲酰基-2-甲氧基萘3a是主要产物。使用InCl3和相应的酰氯2b-e代替2a可以选择性地得到2-酰基-6-甲氧基萘4b-e。在化学计量比的InCl3存在下，即使在50°C下，1与2a的反应也得到4a和5a作为主要产物。该反应似乎涉及3a到4a和5a的异构化。
The regiochemistry of the reaction of 2-methoxynaphthalene 1 with benzoyl chloride 2a using a catalytic amount of a Lewis acid is strongly influenced by the identity of the acid catalyst employed as well as by the reaction temperature. By using InCl3, FeCl3, SnCl4 or ZnCl2 and heating at 160 °C, 2-benzoyl-6-methoxynaphthalene 4a is selectively produced along with 1-benzoyl-7-methoxynaphthalene 5a, while in the case of AlCl3, SbCl5 or TiCl4, 1-benzoyl-2-methoxynaphthalene 3a is the major product. 2-Acyl-6-methoxynaphthalenes 4b–e can be selectively obtained using InCl3 and the corresponding acyl chlorides 2b–e in place of 2a. In the presence of a stoichiometric amount of InCl3, the reaction of 1 with 2a also gives 4a as the predominant product along with 5a even at 50 °C. This reaction appears to involve isomerisation of 3a to 4a and 5a.