Photochemical Preparation of 1,3,5,7-Tetracyanoadamantane and Its Conversion to 1,3,5,7-Tetrakis(aminomethyl)adamantane

New adamantane derivatives 1 and 2 that bear functionalized one-carbon extensions at all four bridgehead positions have been prepared. Radical nucleophilic substitution (SRN1) reaction of 1,3,5,7-tetrabromoadamantane with cyanide produces 1,3,5,7-tetracyanoadamantane (1), which was reduced with bora...

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Bibliographic Details
Published in:	Organic letters Vol. 6; no. 11; pp. 1705 - 1707
Main Authors:	Lee, Ging S, Bashara, Jude N, Sabih, Ghiwa, Oganesyan, Asmik, Godjoian, Gayane, Duong, Hieu M, Marinez, Eric R, Gutiérrez, Carlos G
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 27-05-2004
Subjects:	Adamantane - analogs & derivatives Adamantane - chemistry Magnetic Resonance Spectroscopy Molecular Structure Photochemistry
Online Access:	Get full text
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Summary:	New adamantane derivatives 1 and 2 that bear functionalized one-carbon extensions at all four bridgehead positions have been prepared. Radical nucleophilic substitution (SRN1) reaction of 1,3,5,7-tetrabromoadamantane with cyanide produces 1,3,5,7-tetracyanoadamantane (1), which was reduced with borane reagents to 1,3,5,7-tetrakis(aminomethyl)adamantane (2). Improvements in the preparation of 1,3,5,7-tetrahaloadamantanes (halogen = Br, Cl, I) are also reported.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol036526g