Method of preparing polycyclic diamines

A process for preparing polycyclic diamines represented by Formula I:

• ##STR19## wherein Y is --CH.sub.2 --, --NR.sup.3' --, --S--, or --O--;
• R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkenyl or alkenylene containing 2 to 20 carbon atoms;
• alkyl or alkylene containing 1 to 20 carbon atoms, aryl or arylene containing 5 to 12 ring atoms in which up to 5 of the ring atoms may be selected from S, Si, N, O, and P heteroatoms;
• cycloalkyl or cycloalkylene containing 3 to 12 ring atoms in which one or more ring atoms may be selected from S, Si, N, O, and P heteroatoms;
• and acyl, wherein acyl is ##STR20## wherein R.sup.4 is described as for R.sup.1 to R.sup.3, and further R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may include functional groups selected from the group consisting of aryl, amide, thioamide, ester, thioester, ketone (including oxo-carbons), thioketone, nitrile, nitro, sulfide, sulfoxide, sulfone, disulfide, tertiary amine, ether, urethane, dithiocarbamate, quarternary ammonium and phosphonium, halogen, silyl, siloxy, wherein the functional groups requiring substituents are substituted with hydrogen, comprising the steps of:
• a) mixing a bispyridine compound, and an electrolyte solution, wherein said electrolyte solution has sufficient acid strength to render said bispyridine compound essentially protonated;
• and is represented by Formula IV ##STR21## wherein Y is --CH.sub.2 --, --NR.sup.3' --, --S--, or --O--;
• each R.sup.3', R.sup.8 and R.sup.9 are independently selected from hydrogen, or lower alkyl having 1 to 4 carbon atoms, and X is a counter-ion selected from a group consisting of chloride, bromide, iodide, sulfate, bisulfate, fluoroborate, perchlorate, and trifluoroacetate;
• and
• b) subjecting said mixture to electroreductive coupling in an electrochemical cell.