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Reaction of a 6‐Dimethylaminopentafulvene with the Mes 2 PCH 2 CH 2 B(C 6 F 5 ) 2 Frustrated Lewis Pair
Author(s) -
Xu BaoHua,
Mömming Cornelia M.,
Fröhlich Roland,
Kehr Gerald,
Erker Gerhard
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101937
Subject(s) - chemistry , hydroboration , isomerization , toluene , derivative (finance) , yield (engineering) , x ray crystallography , crystallography , fulvene , thermal decomposition , stereochemistry , medicinal chemistry , diffraction , catalysis , organic chemistry , materials science , physics , financial economics , economics , metallurgy , optics
Abstract The frustrated Lewis pair Mes 2 PCH 2 CH 2 B(C 6 F 5 ) 2 reacts readily with 6‐dimethylamino‐6‐methylfulvene at room temperature to yield the trans ‐1‐[B(C 6 F 5 ) 2 ]‐2‐[CH 2 CH 2 PMes 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 6 F 5 ) 2 ]‐3‐[CH 2 CH 2 PMes 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 6 F 5 ) 2 yielded the corresponding parent compound 13 that was also characterized by X‐ray diffraction.