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Reactions of Alk‐1‐enylxenonium(II) and Alk‐1‐ynylxenonium(II) Salts [RXe]Y with Bromides and Iodides in Anhydrous HF
Author(s) -
Frohn HermannJosef,
Bardin Vadim V.
Publication year - 2007
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200700075
Subject(s) - chemistry , anhydrous , bromine , medicinal chemistry , iodine , salt (chemistry) , organic chemistry
The replacement of xenon(+) by iodine in reactions of alkenylxenonium(II) salts [RCF=CFXe]Y (R = cis ‐C 2 F 5 , trans ‐H) and alkynylxenonium(II) salt [C 3 F 7 C≡CXe][BF 4 ] with NaI in anhydrous HF (aHF) occurred regiospecifically. At −60 °C the substitution of xenon(+) by bromine in the perfluorinated salts [ cis ‐CF 3 CF=CFXe]Y and [ trans ‐C 4 F 9 CF=CFXe]Y proceeded regio‐ and stereospecifically with NaBr in aHF, but at a higher temperature and after a longer time the treatment of [ cis ‐C 2 F 5 CF=CFXe]Y with NaBr, KBr, or [NBu 4 ]Br in aHF gave mixtures of cis and trans ‐perfluorobut‐1‐enyl bromides. The reaction of [C 3 F 7 C≡CXe][BF 4 ] with NaBr in aHF at −65 °C gave only 48 %, of C 3 F 7 C≡CBr and was accompanied by a mixture of bromine‐containing related olefins. Reaction pathways to the main product are discussed.