Synthesis and conformational studies of 9-methoxy[3.3]metacyclophanes and 9-methoxy[3]metacyclo[3](2,6)pyridinophane

Abstract

anti-9-Methoxy[3]metacyclo [3](2,6)pyridinophan-2,11-dione is obtained by the coupling reaction of 2,6-bis (bromomethyl)pyridine and 2,6-bis[2-isocyano-2-(tolylsulfonyl)ethyl]-4-tert-butylanisole in dimethylformamide (DMF) with an excess of sodium hydride, from which the corresponding syn-9-methoxy[3]metacyclo [3](2, 6)pyridinophane is synthesised via anti-syn-isomerisation during the Wolff-Kishner reduction in good yield.