Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate

We describe the synthesis of alkynyl phosphanes of the type R 2 P–CC–C(OCH 3 )Ph 2 (R = Ph, Cy) and investigate their transformation to geminally substituted phosphonium borato-allene zwitterions upon their reaction with B(C 6 F 5 ) 3 . The mechanism for this transformation was studied experimental...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-08, Vol.57 (67), p.8272-8275
Main Authors: Torres, Lucas C., Dobrovetsky, Roman, Caputo, Christopher B.
Format: Article
Language:English
Subjects:
Crystallography
Density functional theory
Zwitterions
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Summary:We describe the synthesis of alkynyl phosphanes of the type R 2 P–CC–C(OCH 3 )Ph 2 (R = Ph, Cy) and investigate their transformation to geminally substituted phosphonium borato-allene zwitterions upon their reaction with B(C 6 F 5 ) 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03249f