Organometallic nucleophilic ring-opening of endo peroxides

被引:18
作者
Schwaebe, MK [1 ]
Little, RD [1 ]
机构
[1] UNIV CALIF SANTA BARBARA,DEPT CHEM,SANTA BARBARA,CA 93106
关键词
D O I
10.1016/S0040-4039(96)01494-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of symmetrical and unsymmetrical endo peroxides with organometallic reagents affords hydroxy ethers. Primary, secondary, vinyl and aryl groups can be transferred with alkyllithium and Grignard reagents providing the best yields, organozincates, moderate. This demonstrates a new reactivity pattern for endoperoxides and provides a novel method for the formation of a variety of useful building blocks. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6635 / 6638
页数:4
相关论文
共 7 条
[1]   BICYCLIC ENDOPEROXIDES AND SYNTHETIC APPLICATIONS [J].
BALCI, M .
CHEMICAL REVIEWS, 1981, 81 (01) :91-108
[2]   SYNTHESIS OF BICYCLIC GAMMA-LACTONES FROM 2-CYCLOALKENE-1,4-DIOLS [J].
KONDO, K ;
MATSUMOTO, M ;
MORI, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (02) :103-103
[3]   REACTIONS OF GRIGNARD SOLUTIONS .2. ACTION OF THE GRIGNARD REAGENT ON PHOTO-PEROXIDES OF 9-10-DIARYLANTHRACENE [J].
MUSTAFA, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUN) :1662-1663
[4]  
NATSUME M, 1979, TETRAHEDRON LETT, V36, P3473
[5]  
RAZUVAEV GA, 1972, ORGANIC PEROXIDES, V3, P141
[7]  
TREIBS W, 1951, BER, V84, P438