Journal
TETRAHEDRON LETTERS
Volume 46, Issue 28, Pages 4777-4779Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.05.041
Keywords
pentafluorosulfanyl group; nucleophilic substitution; rearrangements
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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.
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