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A Facile Route to 1,3,5,7-Tetraaminoadamantane. Synthesis of 1,3,5,7-Tetranitroadamantane.

ADA100232

Publication Date	1980
Personal Author	Sollott, G. P.; Gilbert, E. E.
Page Count	11
Abstract	1,3,5,7-Tetraaminoadamantane has been prepared from adamantane by a sequence of reactions which by-passes the tetracarboxy derivative, a compound obtained to date in low overall yield via Meerwein ester synthesis and transformation. The key step consisted of the photolysis of the tetraiodide in acetonitrile producing the tetraacetamide. The tetrabromide yielded only the monoacetamide derivative under identical conditions. Although mechanistically similar to the photochemical process, the Ritter reaction was not found to be applicable to the tetraiodide as well as the tetrabromide for obtaining the tetraamide. 1,3,5,7-Tetranitroadamantane was obtained from the tetraamine by permanganate oxidation, a procedure apparently not previously used to prepare compounds with more than two nitro groups.
Keywords	Adamantanes Synthesis(Chemistry) Photolysis Carbonyl compounds Acetonitrile Acetamides Iodides Bromides Photochemical reactions Reprints Permanganates Oxidation Chemical reactions Chemical derivatives Nitro radicals Meerwein reaction Tetraiodide Ritter reaction NTISDODXR
Source Agency	Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	Army Armament Research and Development Command, Dover, NJ. Large Caliber Weapon Systems Lab.; Shared Bibliographic Input Experiment.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v45 n26 p5405-5408, 19 Dec 80.
Document Type	Journal Article
Title Note	Special publication.
NTIS Issue Number	198121

A Facile Route to 1,3,5,7-Tetraaminoadamantane. Synthesis of 1,3,5,7-Tetranitroadamantane.

A Facile Route to 1,3,5,7-Tetraaminoadamantane. Synthesis of 1,3,5,7-Tetranitroadamantane.
ADA100232

Publication Date	1980
Personal Author	Sollott, G. P.; Gilbert, E. E.
Page Count	11
Abstract	1,3,5,7-Tetraaminoadamantane has been prepared from adamantane by a sequence of reactions which by-passes the tetracarboxy derivative, a compound obtained to date in low overall yield via Meerwein ester synthesis and transformation. The key step consisted of the photolysis of the tetraiodide in acetonitrile producing the tetraacetamide. The tetrabromide yielded only the monoacetamide derivative under identical conditions. Although mechanistically similar to the photochemical process, the Ritter reaction was not found to be applicable to the tetraiodide as well as the tetrabromide for obtaining the tetraamide. 1,3,5,7-Tetranitroadamantane was obtained from the tetraamine by permanganate oxidation, a procedure apparently not previously used to prepare compounds with more than two nitro groups.
Keywords	Adamantanes Synthesis(Chemistry) Photolysis Carbonyl compounds Acetonitrile Acetamides Iodides Bromides Photochemical reactions Reprints Permanganates Oxidation Chemical reactions Chemical derivatives Nitro radicals Meerwein reaction Tetraiodide Ritter reaction NTISDODXR
Source Agency	Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	Army Armament Research and Development Command, Dover, NJ. Large Caliber Weapon Systems Lab.; Shared Bibliographic Input Experiment.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v45 n26 p5405-5408, 19 Dec 80.
Document Type	Journal Article
Title Note	Special publication.
NTIS Issue Number	198121