[60]富勒烯与由环氧化物生成的羰基叶立德的新型环加成反应。

Novel cycloaddition reaction of [60]fullerene with carbonyl ylides generated from epoxides.

作者信息

Wang Guan-Wu, Yang Hai-Tao, Wu Ping, Miao Chun-Bao, Xu Yu

机构信息

Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China.

出版信息

J Org Chem. 2006 May 26;71(11):4346-8. doi: 10.1021/jo060427+.

DOI:10.1021/jo060427+

PMID:16709087

Abstract

The thermal reaction of [60]fullerene (C60) with the carbonyl ylides generated in situ from trans-epoxides to give C60-fused tetrahydrofuran derivatives has been investigated. The reaction of C60 with trans-2-benzoyl-3-aryloxiranes afforded only cis-products, while the reaction of C60 with 2-cyano-2-ethoxycarbonyl-3-aryloxiranes gave exclusively or predominantly cis isomers. The isomeric distributions of the latter reactions were drastically affected by the substituent on the phenyl ring.

摘要

研究了[60]富勒烯（C60）与由反式环氧化合物原位生成的羰基叶立德发生热反应生成C60稠合四氢呋喃衍生物的情况。C60与反式-2-苯甲酰基-3-芳基环氧乙烷的反应仅得到顺式产物，而C60与2-氰基-2-乙氧基羰基-3-芳基环氧乙烷的反应则 exclusively 或主要得到顺式异构体。后一种反应的异构体分布受到苯环上取代基的显著影响。