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

School of Chemistry

Tel Aviv University

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

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

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc03249f

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title = "Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate",

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.",

author = "Torres, \{Lucas C.\} and Roman Dobrovetsky and Caputo, \{Christopher B.\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2021",

month = aug,

day = "28",

doi = "10.1039/d1cc03249f",

language = "الإنجليزيّة",

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TY - JOUR

T1 - Allenic phosphonium borate zwitterions

T2 - Via a phosphonium allenylidene intermediate

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.

UR - http://www.scopus.com/inward/record.url?scp=85113729700&partnerID=8YFLogxK

U2 - 10.1039/d1cc03249f

DO - 10.1039/d1cc03249f

M3 - مقالة

C2 - 34323253

SN - 1359-7345

VL - 57

SP - 8272

EP - 8275

JO - Chemical Communications

JF - Chemical Communications

IS - 67

ER -

Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

Abstract

All Science Journal Classification (ASJC) codes

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