Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

Lucas C. Torres; Roman Dobrovetsky; Christopher B. Caputo

doi:10.1039/d1cc03249f

Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

Lucas C. Torres, Roman Dobrovetsky, Christopher B. Caputo^*

^*Corresponding author for this work

School of Chemistry

York University Toronto

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8272-8275
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	67
DOIs	https://doi.org/10.1039/d1cc03249f
State	Published - 28 Aug 2021

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abstract = "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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AU - Torres, Lucas C.

AU - Dobrovetsky, Roman

AU - Caputo, Christopher B.

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2021/8/28

Y1 - 2021/8/28

N2 - 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.

AB - 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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JO - Chemical Communications

JF - Chemical Communications

IS - 67

ER -

Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

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