Mercuracarborand-catalyzed Diels-Alder reactions of a thionoester with cyclopentadiene

被引：48
作者：
Lee, H [1 ]
Diaz, M [1 ]
Hawthorne, MF [1 ]
机构：
[1] Univ Calif Los Angeles, Dept Biochem & Chem, Los Angeles, CA 90095 USA
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 43期
基金：
美国国家科学基金会;
关键词：
carboranes; catalysis; thiocarbonyl compounds; mercury;
D O I：
10.1016/S0040-4039(99)01582-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The multidentate Lewis acids B-octamethyl [12]-mercuracarborand-4 (1) and B-hexamethyl [9]-mercuracarborand-3 (2) catalyze the Diels-Alder reaction of a thionoester 4 with cyclopentadiene. The reaction proceeds more rapidly when catalyzed with 1 and 2 than with monodentate bis(closo-9,12-dimethyl-1,2-carboran-1-yl)mercury (3). Mercury-199 NMR studies demonstrated the formation of a 1:1 complex of 1 with 4 in which the thio function of 4 is coordinated to the HE(II) centers of 1, while the 2.4 and 3.4 complexes are not observed by NMR. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码：7651 / 7655
页数：5
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