I. Trushkov, V. Brel
Jul 11, 2005
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Treatment of 3-chloro-1-pentafluorosulfanylprop-1-ene 1 with KCN yielded the product of prototropic rearrangement ClCH CHCH 2 SF 5 , whereas reactions with NaN 3 and KSCN gave the S N 2 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 .