Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: a mechanism distinct from that postulated previously

被引：12
作者：
Kamata, M
Satoh, C
Kim, HS
Wataya, Y
机构：
[1] Niigata Univ, Fac Educ & Human Sci, Dept Chem, Niigata 9502181, Japan
[2] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 46期
关键词：
1.4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-ene; antimalarial cyclic peroxide; malaria; bicyclic peroxide; FeBr2; rearrangement; diepoxide epoxyketone; mechanism;
D O I：
10.1016/S0040-4039(02)02024-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (la: Ar=p-FC6H4, 1b: Ar=C6H5 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohcxanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c. (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码：8313 / 8317
页数：5
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