Reaction of a 6-dimethylaminopentafulvene with the Mes 2PCH 2CH 2B(C 6F 5) 2 frustrated Lewis Pair

Bao Hua Xu; Cornelia M. Mömming; Roland Fröhlich; Gerald Kehr; Gerhard Erker

doi:10.1002/chem.201101937

Reaction of a 6-dimethylaminopentafulvene with the Mes ₂PCH ₂CH ₂B(C ₆F ₅) ₂ frustrated Lewis Pair

Bao Hua Xu
, Cornelia M. Mömming
, Roland Fröhlich
, Gerald Kehr
, Gerhard Erker^*

^*Corresponding author for this work

University of Münster

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

11 Citations (Scopus)

Abstract

The frustrated Lewis pair Mes ₂PCH ₂CH ₂B(C ₆F ₅) ₂ reacts readily with 6-dimethylamino-6-methylfulvene at room temperature to yield the trans-1-[B(C ₆F ₅) ₂]-2-[CH ₂CH ₂PMes ₂] disubstituted fulvene derivative 9 that features an internal N-B contact. Thermolysis (80 °C in toluene) results in a complete isomerization to the respective 1-[B(C ₆F ₅) ₂]-3-[CH ₂CH ₂PMes ₂] isomer 10. Both compounds were characterized by using X-ray diffraction. A reaction scheme is formulated to rationalize the specific formation of these compounds, involving a retro-hydroboration/hydroboration sequence. The reaction of the 6-dimethylaminofulvene with HB(C ₆F ₅) ₂ yielded the corresponding parent compound 13 that was also characterized by X-ray diffraction.

Original language	English
Pages (from-to)	1826-1830
Number of pages	5
Journal	Chemistry - A European Journal
Volume	18
Issue number	6
DOIs	https://doi.org/10.1002/chem.201101937
Publication status	Published - 6 Feb 2012
Externally published	Yes

Keywords

X-ray diffraction
frustrated Lewis pair
hydroboration
reaction mechanisms
retro-hydroboration

Access to Document

10.1002/chem.201101937

Cite this

@article{47615857d7dd406d8eceac27c9231268,

title = "Reaction of a 6-dimethylaminopentafulvene with the Mes 2PCH 2CH 2B(C 6F 5) 2 frustrated Lewis Pair",

abstract = "The frustrated Lewis pair Mes 2PCH 2CH 2B(C 6F 5) 2 reacts readily with 6-dimethylamino-6-methylfulvene at room temperature to yield the trans-1-[B(C 6F 5) 2]-2-[CH 2CH 2PMes 2] disubstituted fulvene derivative 9 that features an internal N-B contact. Thermolysis (80 °C in toluene) results in a complete isomerization to the respective 1-[B(C 6F 5) 2]-3-[CH 2CH 2PMes 2] isomer 10. Both compounds were characterized by using X-ray diffraction. A reaction scheme is formulated to rationalize the specific formation of these compounds, involving a retro-hydroboration/hydroboration sequence. The reaction of the 6-dimethylaminofulvene with HB(C 6F 5) 2 yielded the corresponding parent compound 13 that was also characterized by X-ray diffraction.",

keywords = "X-ray diffraction, frustrated Lewis pair, hydroboration, reaction mechanisms, retro-hydroboration",

author = "Xu, \{Bao Hua\} and M{\"o}mming, \{Cornelia M.\} and Roland Fr{\"o}hlich and Gerald Kehr and Gerhard Erker",

year = "2012",

month = feb,

day = "6",

doi = "10.1002/chem.201101937",

language = "English",

volume = "18",

pages = "1826--1830",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "6",

}

TY - JOUR

T1 - Reaction of a 6-dimethylaminopentafulvene with the Mes 2PCH 2CH 2B(C 6F 5) 2 frustrated Lewis Pair

AU - Xu, Bao Hua

AU - Mömming, Cornelia M.

AU - Fröhlich, Roland

AU - Kehr, Gerald

AU - Erker, Gerhard

PY - 2012/2/6

Y1 - 2012/2/6

N2 - The frustrated Lewis pair Mes 2PCH 2CH 2B(C 6F 5) 2 reacts readily with 6-dimethylamino-6-methylfulvene at room temperature to yield the trans-1-[B(C 6F 5) 2]-2-[CH 2CH 2PMes 2] disubstituted fulvene derivative 9 that features an internal N-B contact. Thermolysis (80 °C in toluene) results in a complete isomerization to the respective 1-[B(C 6F 5) 2]-3-[CH 2CH 2PMes 2] isomer 10. Both compounds were characterized by using X-ray diffraction. A reaction scheme is formulated to rationalize the specific formation of these compounds, involving a retro-hydroboration/hydroboration sequence. The reaction of the 6-dimethylaminofulvene with HB(C 6F 5) 2 yielded the corresponding parent compound 13 that was also characterized by X-ray diffraction.

AB - The frustrated Lewis pair Mes 2PCH 2CH 2B(C 6F 5) 2 reacts readily with 6-dimethylamino-6-methylfulvene at room temperature to yield the trans-1-[B(C 6F 5) 2]-2-[CH 2CH 2PMes 2] disubstituted fulvene derivative 9 that features an internal N-B contact. Thermolysis (80 °C in toluene) results in a complete isomerization to the respective 1-[B(C 6F 5) 2]-3-[CH 2CH 2PMes 2] isomer 10. Both compounds were characterized by using X-ray diffraction. A reaction scheme is formulated to rationalize the specific formation of these compounds, involving a retro-hydroboration/hydroboration sequence. The reaction of the 6-dimethylaminofulvene with HB(C 6F 5) 2 yielded the corresponding parent compound 13 that was also characterized by X-ray diffraction.

KW - X-ray diffraction

KW - frustrated Lewis pair

KW - hydroboration

KW - reaction mechanisms

KW - retro-hydroboration

UR - https://www.scopus.com/pages/publications/84856325010

U2 - 10.1002/chem.201101937

DO - 10.1002/chem.201101937

M3 - Article

AN - SCOPUS:84856325010

SN - 0947-6539

VL - 18

SP - 1826

EP - 1830

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 6

ER -

Reaction of a 6-dimethylaminopentafulvene with the Mes ₂PCH ₂CH ₂B(C ₆F ₅) ₂ frustrated Lewis Pair

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this