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7460468 
Journal Article 
Practical preparation methods for highly active azaadamantane-nitroxyl- radical-type oxidation catalysts 
Shibuya, M; Sasano, Y; Tomizawa, M; Hamada, T; Kozawa, M; Nagahama, N; Iwabuchi, Y 
2011 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
21 
3418-3425 
English 
We have recently disclosed that a less hindered class of nitroxyl radicals, i.e., 2-azaadamantan-N-oxyl (AZADO), 1-Me-AZADO, and 9-azabicyclo[3.3.1]nonan- N-oxyl (ABNO), exhibit marked catalytic activity for the oxidation of alcohols with the aid of environmentally friendly oxidants, offering a green and sustainable option for current alcohol oxidation. Encouraged by their outstanding catalytic performance, we envisioned the development of scalable routes to these radicals that could be extended to the commercialization of these radicals for benchtop use as well as for industrial use as optional reagents that complement TEMPO, the flagship compound of stable nitroxyl radicals. We herein describe short and reproducible preparation methods for AZADO and 1-Me-AZADO, featuring an efficient construction of the 2-azaadamantane skeleton. 1 Introduction 2 1-Me-AZADO and AZADO: First-Generation Syntheses 3 Second-Generation Synthesis of 1-Me-AZADO 4 Synthetic Venture towards 2-Azaadamantane: Second-Generation Synthesis of AZADO 5 Conclusion. © Georg Thieme Verlag Stuttgart. 
adamantane; alcohol oxidation; hydroamination; nitroxyl radical; organocatalyst; Adamantanes; Alcohol oxidation; hydroamination; Nitroxyl radical; Organocatalysts; Catalyst activity; Industrial applications; Oxidation; Catalytic oxidation; 1 methyl 2 azaadamantan n oxyl; 2 azaadamantan n oxyl; 2 azaadamantane; 7 methylenebicyclo[3.3.1]nonan 3 one oxime; 9 azabicyclo[3.3.1]nonan n oxyl; adamantane derivative; alcohol; azadamantane nitroxyl; benzyl(7 methylenebicyclo[3.3.1]nonane 3 yl)carbamate; chemical compound; endo bicyclo[3.3.1]non 6 ene 3 carboxylic acid; n (benzyloxycarbonyl) 1 methyl 2 azaadamantane; n (benzyloxycarbonyl)endo bicyclo[3.3.1]non 6 en 3 ylamine; unclassified drug; article; catalyst; chemical analysis; chemical composition; chemical interaction; chemical reaction; chemical structure; controlled study; oxidation; structure analysis; synthesis 
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