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Communication | Special issue | Vol 5, No. 1, 1976, pp.299-323
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0299
Synthesis and Circular Dichroism of Some trans-5,5a,6,7,8,9,9a,10-Octahydrobenzo[g]quinoxalines (Octahydrobenzo[g]quinoxalines)

Günther Snatzke* and György Hajós

*Lehrstuhl für Strukturchemie, Ruhr-Universität Bochum, Postfach 10 21 48, D-4630 Bochum 1, Germany


Starting from trans-decalone-2 several optically active pyrazine derivatives with chiral second sphere have been prepared. The cd of the parent compound, 5,5a,6,7,8,9,9a,10-octahydrobenzo[g]quinoxaline (+)-VII reveals four Cotton effects (in isooctane:band I at 327 nm, band II at 270 nm, band III at 228 nm, band IV at 210 nm) which could be assigned to transitions to the following excited states: 1B3u, 1B2u, 1B2g, and 1B1u. The signs of these Cotton effects can be correlated with those of related octahydroanthracenes and ketones with chiral second sphere. The cd spectra of the mono and diprotonated compound support this assignements. The cd spectra of several 2-substitution products are given.