Allenic Phosphonium Borate Zwitterions via a Transient Phosphonium Allenylidene

18 June 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We describe the synthesis of alkynyl phosphanes of the type R2P-C≡C-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.

Keywords

methylene phosphonium
Lewis Acid Rearrangement
alkynyl phosphanes

Supplementary materials

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Allenic Phosphonium Borate Zwitterions via a Transient Phosphonium Allenylidene SI
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