Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides

Authors
Clayden, J McCarthy, C Helliwell, M
Citation
J. Clayden et al., Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides, CHEM COMMUN, (20), 1999, pp. 2059-2060
Citations number
17
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
20
Year of publication
1999
Pages
2059 - 2060
Database
ISI
SICI code
1359-7345(1999):20<2059:BPGTRO>2.0.ZU;2-3
Abstract
8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds a t room temperature, and the rate at which they racemise (by rotation about the Ar-CO bond) depends principally on the extent to which the 8-substituen t undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.