2,4,8,10-Tetrabromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

Abstract

Key indicatorsSingle-crystal X-ray study T = 150 K Mean (C-C) = 0.005 Å R factor = 0.024 wR factor = 0.053 Data-to-parameter ratio = 19.2 For details of how these key indicators were automatically derived from the article, see

Synthesis of Symmetric Dinitro‐Functionalised Tröger's Base Analogues

“…The structure of 31 was confirmed by X-ray crystallography. [16] This is yet another example of a Tröger's base compound that is multiply-substituted with electron-withdrawing substituents, the others being analogues with substituent patterns like 4,10-dichloro-1,7-dimethoxy-2,8-dimethyl ester, [17] 4,10-dibromo-2,8-diethyl ester, [18] tetrahalo, [9,13,19] and octafluoro [20] . In the present case, it is thought that the electron-withdrawing nature of the two nitro groups in the aniline should be offset somewhat by the methyl and methoxy groups that are also expected to aid in the solubility of 31.…”

1,7-Dibromo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

“…The presence of the methano strap between the two N atoms in the diazocine ring prevents pyramidal inversion and permits resolution of the enantiomers (Prelog & Wieland, 1944). This dihedral angle has been measured across a range of compounds to lie between 82 (Solano et al, 2005) and 108 (Faroughi et al, 2006) for simple dibenzo Trö ger's base analogues. This dihedral angle has been measured across a range of compounds to lie between 82 (Solano et al, 2005) and 108 (Faroughi et al, 2006) for simple dibenzo Trö ger's base analogues.…”

3,9-Dibromo-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

“…Trö ger's base (Trö ger, 1887) is a chiral C 2 -symmetric molecule that owes its chirality to the presence of the two tertiary N atoms in the bridge (Spielman, 1935). This bridging unit imparts a twist within the molecule and the resultant dihedral angle has been measured across a range of compounds to lie between 82 (Solano et al, 2005) and 108 (Faroughi et al, 2006) for simple dibenzo Trö ger's base analogues. Compound (I) ( Fig.…”