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

页码：4777 / 4779

页数：3

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