Sterically crowded hexaalkyl benzene-1,2,3,4,5,6-hexakis[alpha-(alkoxycarbonyl)propanoates]. Synthesis and conformation analysis

Authors
Alexander, D Bohm, S Cisarova, I Holy, P Podlaha, J Slouf, M Zavada, J
Citation
D. Alexander et al., Sterically crowded hexaalkyl benzene-1,2,3,4,5,6-hexakis[alpha-(alkoxycarbonyl)propanoates]. Synthesis and conformation analysis, COLL CZECH, 65(5), 2000, pp. 673-694
Citations number
24
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
65
Issue
5
Year of publication
2000
Pages
673 - 694
Database
ISI
SICI code
0010-0765(200005)65:5<673:SCHB>2.0.ZU;2-U
Abstract
A selective hexa-fold monoalkylation of the malonester carbanion (-)CH(COOR )(2) (R = Me, Et, t-Bu, Bn) with hexakis(bromomethyl)benzene afforded the t itle compounds 3 in a high-yield reactions. On subsequent replacement of th e acid a-hydrogens with bulkier substituents, the title compounds 3, R = Et , provided a broad variety of the alpha-X-persubstituted homologues and der ivatives 4 (X = Me, Et, Bu, Oc, Bn, Br, N-3). The effect of the variable X substituent on conformation was investigated by single-crystal X-ray diffra ction and compared with the results obtained by theoretical calculation.