Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

Anne-Frederique Pecharman; Michael Hill; Claire McMullin; Mary Mahon

doi:10.1002/anie.201709902

Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

Anne-Frederique Pecharman, Michael Hill, Claire McMullin, Mary Mahon

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

28 Citations (SciVal)

5 Downloads (Pure)

Abstract

Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.

Original language	English
Pages (from-to)	16363-16366
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	51
Early online date	27 Nov 2017
DOIs	https://doi.org/10.1002/anie.201709902
Publication status	Published - 13 Dec 2017

Access to Document

10.1002/anie.201709902Licence: CC BY

Augmentation of Alkaline Earth Reactivity: An FLP Analogy
Hill, M. (PI)
Engineering and Physical Sciences Research Council
8/02/16 → 6/02/20
Project: Research council

Michael Hill
- M.S.Hillbath.acuk
Person: Research & Teaching, Affiliate staff

Balena High Performance Computing (HPC) System
Facility/equipment: Equipment
High Performance Computing (HPC) Facility
Chapman, S. (Manager)
University of Bath
Facility/equipment: Facility

Cite this

@article{2a7c469b2cb64f24a3eb38c6d3ac0b05,

title = "Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization",

abstract = "Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.",

author = "Anne-Frederique Pecharman and Michael Hill and Claire McMullin and Mary Mahon",

year = "2017",

month = dec,

day = "13",

doi = "10.1002/anie.201709902",

language = "English",

volume = "56",

pages = "16363--16366",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Inc.",

number = "51",

}

TY - JOUR

T1 - Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

AU - Pecharman, Anne-Frederique

AU - Hill, Michael

AU - McMullin, Claire

AU - Mahon, Mary

PY - 2017/12/13

Y1 - 2017/12/13

N2 - Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.

AB - Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3B, provide facile B-B' single bond formation. Although the Ph3B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.

U2 - 10.1002/anie.201709902

DO - 10.1002/anie.201709902

M3 - Article

SN - 1433-7851

VL - 56

SP - 16363

EP - 16366

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 51

ER -

Magnesium Boryl Reactivity with 9-BBN and Ph3B: Rational B-B' Bond Formation and Diborane Isomerization

Abstract

Access to Document

Fingerprint

Projects

Augmentation of Alkaline Earth Reactivity: An FLP Analogy

Profiles

Michael Hill

Equipment

Balena High Performance Computing (HPC) System

High Performance Computing (HPC) Facility

Cite this