Naphthalene-based calixarenes: unusual regiochemistry of a Friedel-Crafts alkylation.
Naphthalene-based calixarenes: unusual regiochemistry of a Friedel-Crafts alkylation.
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基于萘的杯芳烃：弗里德尔-克来福特烷基化的不寻常区域化学。
DOI：
10.1021/ol006980
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发表时间：
2001
期刊：
影响因子：
5.2
通讯作者：
T. Glass
中科院分区：
文献类型：
--
作者：
B. J. Shorthill;T. Glass
[反应：见正文]在萘基杯芳烃的研究中，观察到具有不寻常区域化学的Friedel-Crafts烷基化反应。用催化三氟甲磺酸处理甲醇14预期产生由16表示的类别的杯芳烃。相反，主要产物是环状三聚体15，其中每个萘环的烷基化发生在电子失活位置。化合物15的结构通过2-D NMR确定。
[reaction: see text] In the pursuit of naphthalene-based calixarenes, a Friedel-Crafts alkylation with unusual regiochemistry was observed. Treatment of carbinol 14 with catalytic triflic acid was expected to produce calixarenes of the class represented by 16. Instead, the major product was cyclic trimer 15, in which alkylation of each naphthalene ring occurred at the electronically deactivated position. The structure of compound 15 was assigned by 2-D NMR studies.