M. Westerhausen, Tobias Bollwein, K. Karaghiosoff
Feb 5, 2002
Citations
0
Influential Citations
12
Citations
Journal
Organometallics
Abstract
The protonation of racemic (1S,2S)-bis(methylzinc) and (1R,2R)-bis(methylzinc) 1,2-bis((trialkylsilyl)amido)-1,2-dipyridylethane (2) with acetamide quantitatively yields racemic 1,2-bis((trialkylsilyl)amino)-1,2-dipyridylethane (3); the meso form 4 is not observed. Irradiation of 3 leads to an equilibrium mixture of all possible isomers, which have been detected by NMR spectroscopy. The crystal structures of 3 and 4 show elongated C−C bonds of the ethane backbone. Recrystallization of 3 from a water/acetone mixture resulted in precipitation of a water adduct of 3, which crystallizes in a chain structure with weak hydrogen bridges. The reaction of 2 with aniline gave bis(methylzinc) 1,2-bis(phenylamido)-1,2-dipyridylethane (5). Experiments with 15N-labeled aniline show that, however, the C−N, not the Si−N, bonds are cleaved.