Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-sigma and p-pi interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes

Authors
Gurskii, ME Gueiderikh, AV Bubnov, YN Antipin, MY Lyssenko, KA Gridnev, ID Boese, R Blaeser, D
Citation
Me. Gurskii et al., Conformational behavior of 3-borabicyclo[3.3.1]nonanes. Intramolecular p-sigma and p-pi interactions in 3,7-endo-disubstituted 3-borabicyclo[3.3.1]nonanes, J ORGMET CH, 636(1-2), 2001, pp. 3-6
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANOMETALLIC CHEMISTRY
ISSN journal
0022328X → ACNP
Volume
636
Issue
1-2
Year of publication
2001
Pages
3 - 6
Database
ISI
SICI code
0022-328X(20011125)636:1-2<3:CBO3IP>2.0.ZU;2-M
Abstract
Intramolecular interactions between the unoccupied p-orbital of the boron a tom and the sigma- (Me) or pi -orbital (Ph) of the 7-endo-substituent lead to an unusual stability of the chair-chair conformation in 3-borabicyclo[3. 3.1]nonanes. X-ray analysis of 3,7 alpha -dimethyl-3-borabicyclo[3.3.1]nona ne (7) and 3-methyl-7 alpha -phenyl-3-borabicyclo[3.3.1]nonane (8), and sin gle point ab initio calculation (B3LYP/6-31G*) of 8 have confirmed the exis tence of this specific attractive interaction. (C) 2001 Elsevier Science B. V. All rights reserved.