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Synthesis, Structures and Reactivity of N ‐Borane‐Protected 1,1′‐Bisimidazoles with Different Bridging Functions
Author(s) -
Weiss Andre,
Pritzkow Hans,
Siebert Walter
Publication year - 2002
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/1099-0682(200207)2002:7<1607::aid-ejic1607>3.0.co;2-5
Subject(s) - chemistry , borane , deprotonation , methane , bridging (networking) , reactivity (psychology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , ion , computer network , alternative medicine , pathology , computer science
The bridging functions Me 2 Si, [(CH 2 ) 3 (CMe 2 ) 2 N]B and CH 2 have been used to connect two imidazoles in the 1,1′‐position. The bisimidazolyl compounds were treated with BH 3 or BEt 3 , and the resulting N , N ′‐bisborane‐protected products 1 , 3b , 4a , and 5b were characterized by X‐ray structure analyses. Reaction of 1,1′‐bis(4,5‐dimethylimidazolyl)methane with BBr 3 yielded the macrocyclic dicationic tetraimidazolyl compound 6 . The behavior of the N‐protected bisimidazoles 1 and 3 − 5 towards deprotonating agents was investigated and it was found that 1,1′‐bis(3‐borane‐4,5‐dimethylimidazolyl)methane ( 5b ) is deprotonated to give a dianionic dicarbene compound. Its reaction with Cp 2 MCl 2 allowed the formation of the corresponding titanocene and zirconocene complexes 8 and 9 , which were characterized by X‐ray structure analyses. In 9 a 3c,2e B−H−Zr bond is present. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)