Synthese und Struktur eines hochsubstituierten Tetracyclo[3.3.0.02,8.04,6]octans (Nortriasteran)

Das 4,8-Dibrombicyclo[3.3.0]octa-2,6-dien-2,6-dicarbonitril 2 reagiert mit Natriummethanolat in Methanol quantitativ und vollstandig stereoselektiv zum Nortriasterandicarbonitril 5. Dieses kristallisiert triklin in der Raumgruppe P1 mit zwei enantiomorphen Molekulen in der Elementarzelle. Einige geometrische Parameter der Cyclopropanringe und der Bildungsmechanismus von 5 werden diskutiert. Synthesis and Structure of a Highly Substituted Tetracyclo[3.3.0.02,8.04,6]octane (Nortriasterane) The 4,8-dibromobicyclo[3.3.0]octa-2,6-diene-2,6-dicarbonitrile 2 reacts with sodium methoxide in methanol quantitatively and with complete stereoselectivity to afford the nortriasteranedicarbonitrile 5. This dinitrile crystallizes triclinically in the space group P1 with two enantiomorphous molecules per cell. Some geometric parameters involving the cyclopropane rings and the mechanism of formation of 5 are discussed.

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