Abstract: First examples of alk-1-yn-1-yliodine(V) molecules, CF3C CIF4 and C6F13C CIF4, were prepared by fluorination of the corresponding 1-iodoperfluoroalk-1-ynes with XeF2 in 1,1,1,3,3-pentafluorobutane (PFB) in the presence of BF3. The reaction of 1-iodo-2-(4-heptafluorotolyl)ethyne, 4-CF3C6F4C CI, with XeF2 (1.5 equiv) and BF3 resulted in a mixture of 4-CF3C6F4C CIF2 (main product), 4-CF3C6F4C CIF4, and trans-(4-CF3C6F4)CF=CFI, whereas under the action of 3 equiv of XeF2/BF3 a complex mixture of polyfluoroorganics and IF5 resulted. Non-fluorinated C4H9C CI reacted with XeF2/BF3 preferentially under fluorine addition across the triple bond and gave mainly C4H9CF2CF2I. The differing reactivity of CnF2n+1C CI and C4H9C CI is in accordance with the experimentally proved different reactivity of the triple bond in C6F13C CH and C4H9C CH toward XeF2/BF3 in PFB. Compound C6F13C CH was inert whereas C4H9C CH was converted into C4H9CF2CF2H (main product) under the same conditions. (C) 2013 Elsevier B.V. All rights reserved.

Cite: Bardin V.V. , Frohn H-J.
Preparation of first examples of RFC CIF4 molecules. A study of the fluorination of selected 1-iodoalk-1-ynes with xenon difluoride/boron trifluoride
Journal of Fluorine Chemistry. 2013. V.146. P.98-104. DOI: 10.1016/j.jfluchem.2013.01.006 WOS Scopus РИНЦ

Dates:

Published print:

Feb 1, 2013

Identifiers:

Web of science	WOS:000316588000015
Scopus	2-s2.0-84873732461
Elibrary	20433707
OpenAlex	W2950733502

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