OPTICALLY-ACTIVE AROMATIC SPIRANES .18. S YNTHESES OF OPTICALLY-ACTIVE 4,4'-DISUBSTITUTED 2,2'-SPIROBI-S-HYDRINDACENES .1.

Citation
M. Melmer et al., OPTICALLY-ACTIVE AROMATIC SPIRANES .18. S YNTHESES OF OPTICALLY-ACTIVE 4,4'-DISUBSTITUTED 2,2'-SPIROBI-S-HYDRINDACENES .1., Monatshefte fuer Chemie, 126(8-9), 1995, pp. 933-943
Citations number
13
Categorie Soggetti
Chemistry
Journal title
ISSN journal
00269247
Volume
126
Issue
8-9
Year of publication
1995
Pages
933 - 943
Database
ISI
SICI code
0026-9247(1995)126:8-9<933:OAS.SY>2.0.ZU;2-A
Abstract
All optically active title compounds were obtained from the 4,4'-diace tyl-spiro compound 2; (+)- and (-)-2 were accessible by chromatography on triacetyl cellulose in ethanol. The enantiomeric purities were est ablished from chromatographic data. The chirality(-)-(2R) was deduced for all new compounds on the basis of the CD spectra of (-)-2 and )-2, 2'-spirobi-(5,6,7,8-tetrahydrobenzo[f]indane). From the molar rotation s of these 4,4'-disubstituted 2,2'-spirobiindanes (empirical) ligand p arameters lambda were determined (using the so-called ''shortened appr oach''). Generally, the values of lambda in these com pounds are highe r than those of the analogous tetrahydrobenzoindane derivatives.