Unusual reactivity of 3-chloro-1-pentafluorosulfanylpropene in nucleophilic substitution reactions

被引：20
|
作者：
Trushkov, IV
Brel, VK [1 ]
机构：
[1] Russian Acad Sci, Inst Physiol Act Cpds, Chernogolovka 142432, Russia
[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 28期
关键词：
pentafluorosulfanyl group; nucleophilic substitution; rearrangements;
D O I：
10.1016/j.tetlet.2005.05.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 3-chloro-1-pentafluorosulfanylprop-1-ene 1 with KCN yielded the product of prototropic rearrangement CICH=CHCH2SF5, whereas reactions with NaN3 and KSCN gave the SN2 products. Ab initio calculations at MP2/6-311++G** level are used to explain the unusual behaviour of cyanide. It was found that proton transfers from both 1 to CN- and from HCN to the anion of 1 are exothermic. In contrast, azide and thiocyanate ions are too weakly basic to deprotonate 1. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4777 / 4779
页数：3
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