CARBENOID REACTIONS OF TRIFLUOROMETHYLELEMENT COMPOUNDS .2. THE REACTIONS OF BIS(TRIFLUOROMETHYL) CADMIUM COMPLEXES WITH CYCLIC ETHERS AND THIOETHERS - A CD-113 NMR AND F-19 NMR-STUDY OF THE INTERMEDIATES

The reactions of Cd(CF3)(2) . 2CH(3)CN with tetrahydrofuran (THF), tetrahydrothiophene and tetrahydrothiopyran in the presence of BF3 . CH3CN yield open-chain difluoromethyl ethers and thioethers. The final product from the reaction with tetrahydrothiophene, [4-(difluoromethylthio)butyl] tetrahydrot...

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Published inJournal of fluorine chemistry Vol. 73; no. 2; pp. 229 - 235
Main Authors MOCKEL, R, TYRRA, W, NAUMANN, D
Format Journal Article
LanguageEnglish
Published LAUSANNE 1 Elsevier 01.08.1995
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
MECHANISM
DIFLUOROCARBENE
MASS SPECTROMETRY
DIFLUOROMETHYL ETHER
DIFLUOROMETHYL THIOETHERS
GEM-DIFLUOROCYCLOPROPANES
NMR SPECTROSCOPY
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Summary:The reactions of Cd(CF3)(2) . 2CH(3)CN with tetrahydrofuran (THF), tetrahydrothiophene and tetrahydrothiopyran in the presence of BF3 . CH3CN yield open-chain difluoromethyl ethers and thioethers. The final product from the reaction with tetrahydrothiophene, [4-(difluoromethylthio)butyl] tetrahydrothiophenium tetrafluoroborate, has been fully characterized, whereas the products of the reactions with THF yielded polymeric ethers containing the OCF2H group. All cadmium-containing intermediates formed during the reaction with tetrahydrothiophene could be detected by Cd-113 and F-19 MMR spectroscopy indicating that a carbenoid mechanism is more likely than a 'free' difluorocarbene mechanism. In contrast to the reactions of the trifluoromethylcadmium derivative with THF in the presence of BF3, reactions in the presence of BCl3 or InCl3 yielded 4-chlorobutyl(difluoromethyl) ether.
ISSN:0022-1139
DOI:10.1016/0022-1139(94)03221-K