BENZENE-RING FLIPPING IN SYN[2.2]METACYCLOPHANES - EFFECT OF SUBSTITUENTS

Authors
ITO S NAKASATO Y HIOKI H NAGAKU M KAN Y FUKAZAWA Y
Citation
S. Ito et al., BENZENE-RING FLIPPING IN SYN[2.2]METACYCLOPHANES - EFFECT OF SUBSTITUENTS, Tetrahedron letters, 34(23), 1993, pp. 3789-3792
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
23
Year of publication
1993
Pages
3789 - 3792
Database
ISI
SICI code
0040-4039(1993)34:23<3789:BFIS-E>2.0.ZU;2-7
Abstract
5-Formyl-13-methyl- and 5,13-diformyl-syn[2.2]metacyclophanes were syn thesized. Their electronic spectra, DELTAH(not-equal) for their benzen e ring flipping, and the result of molecular orbital calculations were compared with those of the 5,13-dimethyl derivative, with the conclus ion that Coulombic repulsion between two benzene rings is the major fa ctor controlling the stability of syn conformers.