REDUCTIVE DEBENZYLATION OF 2,4,6,8,10,12-HEXAAZAISOWURTZITANE

A high-pressure liquid chromatography-mass spectroscopy (HPLC-MS) study of the product composition from the catalytic hydrogenolysis of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane (HBIW) and 4,10-dibenzyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (DBTA) was undertaken. The hydrogenolysis of HBIW is observed in all possible directions. Debenzylation of DBTA in formic acid results in forming the mixture of 4,10-diformyl-2,6,8,12tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (DFTA), 4-formyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (FTA), and 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TA), the contents of which depend on the CHOOH concentration. In aqueous solutions of formic acid the process is complicated by hydrolysis of the amide groups. Some of the hydrolysis products keep the structure of 2,4,6,8,10,12-hexaazaisowurtzitane. Debenzylation of DBTA in mixtures of formic/acetic, formic/propionic, or formic/iso-butyric acids leads to the same mixed products. The procedure of palladium catalyst reuse in the two-stage reductive debenzylation of HBIW was developed and is presented.