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Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

Chemical Communications, ISSN: 1364-548X, Vol: 57, Issue: 67, Page: 8272-8275
2021
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We describe the synthesis of alkynyl phosphanes of the type R2P-CC-C(OCH3)Ph2 (R = Ph, Cy) and investigate their transformation to geminally substituted phosphonium borato-allene zwitterions upon their reaction with B(C6F5)3. The mechanism for this transformation was studied experimentally and by density functional theory computations (DFT), suggesting the intermediacy of an unsaturated 3-coordinate phosphonium electrophile akin to a methylene phosphonium cation.

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