Journal
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE
Volume 646, Issue 13, Pages 784-789Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/zaac.202000047
Keywords
Fluorination; Fluorophosphorane; Phosphonium phosphate; Perfluoropropenyl; Phosphonium stannate
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In this contribution we report on fluorotrimethyl[(Z)-pentafluoropropen-1-yl]phosphorane as a phosphorus based fluorinating reagent. Its solid state structure can be described as a trigonal bipyramid featuring elongated axial bonds due to the formation of a 3-center 4-electron bond. Abstraction of the fluoride ion leads to a shortening of the axial P-C bond. Thus the title compound can be utilized for substitution of bromine with fluorine and for the transfer of fluoride ions onto electrophilic compounds. Reaction with Sn(C2F5)(2)Br(2)afforded salt [P(CH3)(3)(C3F5)](2)[Sn(C2F5)(2)F-4]. When fluorotrimethyl[(Z)-pentafluoropropen-1-yl]phosphorane was treated with P(C2F5)(2)F the primarily produced anion is sufficiently nucleophilic to attack the propenyl group of the cation in beta-position to the phosphorus atom to yield zwitterionic [Me3PCF=C(CF3)-PF3(C2F5)(2)].
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