Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate

We describe the synthesis of alkynyl phosphanes of the type R2P-C C-C(OCH3)Ph-2 (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 b...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 57; no. 67; pp. 8272 - 8275
Main Authors Torres, Lucas C., Dobrovetsky, Roman, Caputo, Christopher B.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.08.2021
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Crystallography
Density functional theory
Physical Sciences
Science & Technology
Zwitterions
DYNAMICS
METHYLENEPHOSPHONIUM ION
VALENCE
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Summary:We describe the synthesis of alkynyl phosphanes of the type R2P-C C-C(OCH3)Ph-2 (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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ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03249f