Synthesis and Chemistry of 1,3,5,7-Tetranitrocubane Including Measurement of Its Acidity, Formation of o-Nitro Anions, and the First Preparations of Pentanitrocubane and Hexanitrocubane1

Autor:	Eric Punzalan, Jianchang Li, Philip E. Eaton, Jürgen Hain, Kirill Lukin, Richard Gilardi, Nobuhiro Kanomata
Rok vydání:	1997
Předmět:	Trimethylsilyl Hydrogen Octanitrocubane chemistry.chemical_element General Chemistry Biochemistry Medicinal chemistry Catalysis Ion chemistry.chemical_compound Colloid and Surface Chemistry chemistry Cubane Electrophile Nitro Vicinal
Zdroj:	Journal of the American Chemical Society. 119:9591-9602
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja970552q
Popis:	Nitro groups on alternate corners of cubane enhance the acidity of cubyl hydrogen (pKa ∼21) and provide sufficient activation for ready anion formation. The sodium salt of 1,3,5,7-tetranitrocubane reacts easily with electrophiles and leads thereby to yet more highly substituted cubanes, like carbomethoxy- and (trimethylsilyl)tetranitrocubane. Anions from these species are also easily formed and are useful for further substitution on the cubane nucleus. Dinitrogen tetraoxide reacts with the anion of tetranitrocubane to give 1,2,3,5,7-pentanitrocubane, the first cubane to contain vicinal nitro groups. The reaction probably involves oxidation of the anion to the corresponding radical. Similarly, the anion of pentanitrocubane is used to prepare 1,2,3,4,5,7-hexanitrocubane, the most highly nitrated cubane made to date. Single-crystal X-ray structural information is given for both penta- and hexanitrocubane.
Databáze:	OpenAIRE
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