Synthesis of macrocycles having tröger base skeletons “[2.2]cyclic tröger base”

2.2]Cyclic Tröger base2 was synthesized by the condensation of 1,2-bis (4-aminopheyl) ethane with paraformaldehyde under acidic condition in 43.8% yield. 2.2]Cyclic Tröger base2 was separated into meso form and racemate by fractional crystallization or using HPLC. Resolution of the racemate into its optical antipodes by passing the racemate through an activated D-(+)-lactose column was partially succeeded.Presented at the 15th Symposium on Structural Organic Chemistry, Kyoto, October, 1982.The trivial name 2.2]cyclic Tröger base is used because of the cumbersome nomenclature.10,12,25,32-Tetraazanonacyclo19.7.7.1^4,8.1^14,18.1^25,32.0^7,12.0^7,12.0^10,15.-0^24,34.0^27,31] octatriaconta-1(29),4,6,8(36),14,16,18(37),21,23,27,-30,34-dodecaene.