Resolution and chiroptical properties of [3(2)](1,4)barrelenophanedicarbonitrile

Authors
Matsuda-Sentou, W Shinmyozu, T
Citation
W. Matsuda-sentou et T. Shinmyozu, Resolution and chiroptical properties of [3(2)](1,4)barrelenophanedicarbonitrile, TETRAHEDR-A, 12(6), 2001, pp. 839-842
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
6
Year of publication
2001
Pages
839 - 842
Database
ISI
SICI code
0957-4166(20010417)12:6<839:RACPO[>2.0.ZU;2-R
Abstract
(+/-)-[3(2)](1,4)Barrelenophane was completely resolved into its enantiomer s by HPLC separation using a chiral stationary phase (Chiralcel OD) with he xane/propan-2-ol (1:9). The specific rotations and circular dichroism spect ra of (+)- and (-)- [3(2)](1.4)barrelenophanes indicated the enantiomeric r elationships. The longest absorption band at 360 nm (epsilon 541, CH2Cl2) i s identified mainly as an intramolecular charge transfer band between the b enzene ring and the double bond conjugated with cyano groups. The X-ray str ucture of the (+)-isomer has been determined. (C) 2001 published by Elsevie r Science Ltd.