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Synthesis and Some Reactions of Hexaazatriphenylenehexacarbonitrile, a Hydrogen-Free Polyfunctional Heterocycle with D(3h) Symmetry.

ADA212298

Publication Date	1986
Personal Author	Kanakarajan, K.; Czarnik, A. W.
Page Count	4
Abstract	In this paper, we report for the first time the synthesis of hexaazatriphenylenehexacarbonitril, abbreviated HAT-hexacarbonitrile. The hydrogenless, symmetrically branched compound can be prepared in analytically pure form on a large scale by using commercially available starting materials. The conversions of HAT-hexacarbonitrile to the corresponding hexaamide, hexaacid, hexaester, and trianhydride derivatives were also accomplished. Our starting material, hexaketocyclohexane octahydrate, is available commercially but is rather expensive. We have therefore prepared it in a two-step reaction from glyoxal; self condensation to afford tetrahydroxyquinone proceeds as described previously, and then oxidation to compound 1 was accomplished by using a modified literature method. Reaction of Hexaketone 1 with an excess of diaminomaleonitrile in refluxing glacial acetic acid affords hexacarbonitrile 3 in 81% yield. Reprints (AW)
Keywords	Nitriles Reaction kinetics Synthesis(Chemistry) Carbon compounds Phenyl radicals Cyclic compounds Ketones Acetic acid Ammino compounds Condensation reactions Maleic acid Materials Reprints Starting Amides Acids Esters Anhydrides Chemical derivatives Cyclohexanes Hydrates Quinones Hydroxyl radicals Hexaazatriphenylenehexacartonitrile Carbonitriles Hexacarbonitriles Nitrile/Hexaazatriphenylenehexacarbo Hexamides Hexaacids Hexaesters Trianhydrides Hexaketocyclohexane Octahydrate Glyoxal Tetrahydroxyquinone Hexaketones Diaminomaleonitrile Maleonitriles Glacial acetic acid
Source Agency	Army Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry
Corporate Authors	Ohio State Univ., Columbus. Dept. of Chemistry.; Army Research Office, Research Triangle Park, NC.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v51 p5241 1986.
Document Type	Journal Article
NTIS Issue Number	199002
Contract Number	DAAG29-85-K-0200

Synthesis and Some Reactions of Hexaazatriphenylenehexacarbonitrile, a Hydrogen-Free Polyfunctional Heterocycle with D(3h) Symmetry.

Synthesis and Some Reactions of Hexaazatriphenylenehexacarbonitrile, a Hydrogen-Free Polyfunctional Heterocycle with D(3h) Symmetry.
ADA212298

Publication Date	1986
Personal Author	Kanakarajan, K.; Czarnik, A. W.
Page Count	4
Abstract	In this paper, we report for the first time the synthesis of hexaazatriphenylenehexacarbonitril, abbreviated HAT-hexacarbonitrile. The hydrogenless, symmetrically branched compound can be prepared in analytically pure form on a large scale by using commercially available starting materials. The conversions of HAT-hexacarbonitrile to the corresponding hexaamide, hexaacid, hexaester, and trianhydride derivatives were also accomplished. Our starting material, hexaketocyclohexane octahydrate, is available commercially but is rather expensive. We have therefore prepared it in a two-step reaction from glyoxal; self condensation to afford tetrahydroxyquinone proceeds as described previously, and then oxidation to compound 1 was accomplished by using a modified literature method. Reaction of Hexaketone 1 with an excess of diaminomaleonitrile in refluxing glacial acetic acid affords hexacarbonitrile 3 in 81% yield. Reprints (AW)
Keywords	Nitriles Reaction kinetics Synthesis(Chemistry) Carbon compounds Phenyl radicals Cyclic compounds Ketones Acetic acid Ammino compounds Condensation reactions Maleic acid Materials Reprints Starting Amides Acids Esters Anhydrides Chemical derivatives Cyclohexanes Hydrates Quinones Hydroxyl radicals Hexaazatriphenylenehexacartonitrile Carbonitriles Hexacarbonitriles Nitrile/Hexaazatriphenylenehexacarbo Hexamides Hexaacids Hexaesters Trianhydrides Hexaketocyclohexane Octahydrate Glyoxal Tetrahydroxyquinone Hexaketones Diaminomaleonitrile Maleonitriles Glacial acetic acid
Source Agency	Army Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry
Corporate Authors	Ohio State Univ., Columbus. Dept. of Chemistry.; Army Research Office, Research Triangle Park, NC.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v51 p5241 1986.
Document Type	Journal Article
NTIS Issue Number	199002
Contract Number	DAAG29-85-K-0200