Masoud Faroughi

Dimethyl 6H,12H-5,11-methano­dibenzo[b,f][1,5]diazo­cine-2,8-diacetate

The asymmetric unit of the title compound, C21H22N2O4, a Tröger’s base analogue derived from methyl 4-aminophenylacetate, contains two crystallographically independent molecules with dihedral angles of 88.44 (5) and 88.68 (6)° between the two benzene rings.

6H,12H-5,11-Ethano­dibenzo[b,f][1,5]diazo­cine

In the molecule of the title compound, C16H16N2, the ethano-strapped analogue of unsubstituted Tröger’s base, the dihedral angle between the two benzene rings is 75.85 (4)°, the smallest angle measured for an ethano-strapped analogue.

6H,12H-5, 11-Methanodibenzo[b,f][1,5]diazocine

Methods for facile synthesis of symmetric and unsymmetric functionalized analogues of Trögers base were developed with use of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (2) as the starting material. C(2)-symmetric 2,8-disubstituted analogues of Trögers base (4a-f) were synthesized via double bromine-lithium exchange of 2 followed by quench with electrophiles. Desymmetrization via single bromine-lithium exchange of 2, followed by quench with electrophiles, afforded asymmetric analogues of Trögers base (6a-g). Further reaction of 2-bromo-8-(trimethylsilyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (6b) produced 7a-c via single bromine-lithium exchange and subsequent quench with electrophiles.

2,8-Dichloro-6H,12H-5,11-ethano-dibenzo[b,f][1,5]diazo-cine.

In the molecule of the title compound, C16H14Cl2N2, the ethano-strapped 2,8-dichloro analogue of Tröger’s base, the dihedral angle between the two benzene rings is 87.01 (3)°.