Allenic phosphonium borate zwitterions: Via a phosphonium allenylidene intermediate

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

doi:https://doi.org/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

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

Access to Document

https://doi.org/10.1039/d1cc03249f

Cite this

@article{59ecb032b9984be39293733c7317b0f6,

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 = "https://doi.org/10.1039/d1cc03249f",

language = "الإنجليزيّة",

volume = "57",

pages = "8272--8275",

number = "67",

}

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 - https://doi.org/10.1039/d1cc03249f

DO - https://doi.org/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

Access to Document

Other files and links

Fingerprint

Cite this