Issue 67, 2021

Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate

Abstract

We describe the synthesis of alkynyl phosphanes of the type R2P–C[triple bond, length as m-dash]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.

Graphical abstract: Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate

Supplementary files

Article information

Article type
Communication
Submitted
18 Jun 2021
Accepted
20 Jul 2021
First published
20 Jul 2021

Chem. Commun., 2021,57, 8272-8275

Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate

L. C. Torres, R. Dobrovetsky and C. B. Caputo, Chem. Commun., 2021, 57, 8272 DOI: 10.1039/D1CC03249F

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