GB1026506A - Bicyclodiamines and preparation thereof - Google Patents

Abstract

The invention comprises diprimary diamines of the formula <FORM:1026506/C2/1> wherein X is a bridgehead carbon atom, R is hydrogen or an alkyl or cycloalkyl group or two R groups on different bridges are joined together to form a single bond connecting the carbon atoms of the two CR2 groups or the R groups of two adjacent CR2 groups in the same bridge are joined together to form a benzene nucleus which includes the carbon atoms of said CR2 groups as adjacent ring carbon atoms, and L, m and n are 1, 2 or 3, the sum of (L + m + n) being from 5 to 9. The diamines may be prepared by converting the corresponding dicarboxylic acids to the acid halides, transforming these to the acyl azides, e.g. with alkali metal azide, and decomposing these by heating to form the diisocyanates, which are then hydrolysed to the diamines. Alternatively, a bicyclic diamine may be made by reducing a corresponding dinitro compound, e.g. with lithium aluminium hydride. 9,10-Diamino-9,10-dihydroendoethano anthracene is prepared by condensing anthraquinone with formamide to give 9,10-bis-formamido-anthracene and half-hydrolysing this to 9-amino-10-formamido-anthracene. The latter is condensed with ethylene to 9-amino-10-formamido-9,10-dihydro-9, 10-endoethano-anthracene which hydrolyses to the diamine. Examples also describe the preparation of the dinitro starting materials by reacting the appropriate bicyclic hydrocarbon with nitrogen dioxide to form first the mononitro compound and then the dinitro compound.