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芳炔亲核捕获的区域选择性:亲核试剂和取代基的电子和空间效应。

Regioselectivity in the nucleophile trapping of arynes: the electronic and steric effects of nucleophiles and substituents.

机构信息

Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.

出版信息

Org Lett. 2014 Jan 3;16(1):6-9. doi: 10.1021/ol403237z. Epub 2013 Dec 6.

DOI:10.1021/ol403237z
PMID:24313272
Abstract

The regioselectivity in nucleophile trapping is investigated with arynes generated directly from bis-1,3-diynes. The regioselectivity is profoundly influenced by not only the nature of nucleophiles but also the substituents on the arynes, which is the consequence of both the unfavorable steric interaction between the incoming nucleophile and the nearby substituent and the inherent electronic bias induced by different substituents on the arynes.

摘要

研究了直接由双 1,3-二炔生成的芳炔中亲核试剂捕获的区域选择性。区域选择性不仅受亲核试剂的性质影响,还受芳炔上取代基的影响,这是由于进入的亲核试剂与附近取代基之间的不利空间相互作用以及芳炔上不同取代基诱导的固有电子偏向的共同结果。

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