Carbonyl groups at positions C2 and C3 enhance stereochemical inversion at C7 in norbornane compounds

被引：4
|
作者：
Jenkins, MN [1 ]
Nash, JJ [1 ]
Morrison, H [1 ]
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期
关键词：
S(N)2 displacement; norbornanes; electric field effect;
D O I：
10.1016/S0040-4039(02)00611-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
It is known that the presence of a carbonyl group at C2 in norbornane compounds aids in the S(N)2 displacement of substituents at C7. In this study, we report a significant enhancement in reactivity at C7 by a second carbonyl group at C3. These diketones undergo rapid inversion at 80degreesC, while the monoketone does not exhibit any reactivity at this temperature. The increase in reactivity is attributed to electric field effects. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3773 / 3775
页数：3
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