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Carbodiphosphorane mediated synthesis of a triflyloxyphosphonium dication and its reactivity towards nucleophiles.

ABSTRACT: A carbodiphosphorane ((Ph₃P)₂C) mediated synthesis of the first triflyloxyphosphonium dication (12+) bearing two electrophilic sites is presented. Depending on the nucleophile, 12+ reacts selectively either at the sulfur atom of the triflyloxy moiety or at the directly attached phosphorus atom. In substitution reactions at the phosphorus atom the triflyloxy moiety serves as a leaving group and enables the synthesis of rare examples of pseudo-halophosphonium dications.

SUBMITTER: Yogendra S

PROVIDER: S-EPMC5433424 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Carbodiphosphorane mediated synthesis of a triflyloxyphosphonium dication and its reactivity towards nucleophiles.

Yogendra S S Hennersdorf F F Bauzá A A Frontera A A Fischer R R Weigand J J JJ

Chemical communications (Cambridge, England) 20170301 20

A carbodiphosphorane ((Ph<sub>3</sub>P)<sub>2</sub>C) mediated synthesis of the first triflyloxyphosphonium dication (12+) bearing two electrophilic sites is presented. Depending on the nucleophile, 12+ reacts selectively either at the sulfur atom of the triflyloxy moiety or at the directly attached phosphorus atom. In substitution reactions at the phosphorus atom the triflyloxy moiety serves as a leaving group and enables the synthesis of rare examples of pseudo-halophosphonium dications. ...[more]

PMID: 28229147

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