Unexpected racemization behavior of 8,8 '-dialkyl-1,1 '-biisoquinoline

Authors
Tsue, H Fujinami, H Itakura, T Hirao, K
Citation
H. Tsue et al., Unexpected racemization behavior of 8,8 '-dialkyl-1,1 '-biisoquinoline, TETRAHEDR-A, 10(15), 1999, pp. 2975-2981
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
15
Year of publication
1999
Pages
2975 - 2981
Database
ISI
SICI code
0957-4166(19990730)10:15<2975:URBO8'>2.0.ZU;2-U
Abstract
The racemization behavior of a series of atropisomeric 8,8'-dialkyl-1,1'-bi isoquinolines, in which methyl, ethyl, and isopropyl groups are introduced for enhancing the transannular steric hindrance, is reported. Contrary to p rior expectations, their configurational stability was inversely proportion al to the steric size of the alkyl groups. (C) 1999 Elsevier Science Ltd. A ll rights reserved.