22734-10-7

Usage

Type of compound

Stable organic nitroso compound

Usage

Organic synthesis, building block for various chemical reactions

Potential applications

Pharmaceuticals, agriculture, material science

Role

Catalyst in various chemical reactions, radical scavenger, antioxidant

Chemical structure

Incorporates both nitroso and adamantane moieties, giving it unique properties and potential applications in research and industry.

InChI:InChI=1/C10H15NO/c12-11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2

Upstream product

• 768-94-5 1-Adamantanamine 
• 281-23-2 adamantane 
• 7575-82-8 1-nitroadamantane 
• 31463-23-7 N-adamantylhydroxylamine 
• 677-22-5 tert-butylmagnesium chloride 

Downstream Products

• 880-52-4 N-(1-adamantyl)acetamide 
• 31463-28-2 N-(Phenylmethylene)tricyclo<3.3.1.1^3,7>decan-1-amine N-Oxide 
• 31463-30-6 N-[(3s,5s,7s)-adamantan-1-yl]-N-phenylhydroxylamine 

Relevant academic research and scientific papers

SYNTHESIS OF DI-t-ALKYLAMINES

Di-t-alkylamines can be synthesized efficiently by a three-step process: (1) oxidation of a t-alkylamine to a t-alkylnitroso compound with peracetic acid in ethyl acetate (2) conversion of the t-alkylnitroso compound to a tri-t-alkylhydroxylamine by successive trapping of two t-butyl radicals and (3) sodium naphthalide reduction to the di-t-alkylamine.

Chemoselectivity of Nitroxylation of Cage Hydrocarbons

Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest

The synthesis and evaluation of new α-hydrogen nitroxides for 'living' free radical polymerization

Three N-alkoxyamines were synthesized for use in nitroxide-mediated radical polymerization. Upon thermolysis, they generate new acyclic α-hydrogen nitroxides: one adamantyl substituted and two diol-containing nitroxides. The initiators were tested in polymerization reactions in direct comparison with the initiator derived from the nitroxide TIPNO. Georg Thieme Verlag Stuttgart.

Azodioxide radical cations

This report provides the first examples of solution-stable azodioxide radical cations and describes their direct spectroscopic observation and, in one case, their thermal chemistry. The formal oxidation potentials, Eo′, for N,N′-dioxo-2,3-diazabicyclo[2.2.2]oct-2-ene (3), N,N′-dioxo-2,3-diazabicyclo[2.2.1]hept-2-ene (4), and N,N′-dioxo-1,1′-azobis(norbornane) (5) are 1.65, 1.68, and 1.54 V vs SCE, respectively. ESR spectroscopy shows the intermediate cations to be π radicals. Radical cation 5?+ (red, λm 510 nm) has a five-line ESR spectrum of a(2N) 1.1 G, while 3?+ (bronze) has a nine-line ESR spectrum simulated as a(4H) 0.86 and a(2N) 1.22 G. Both 3?+ and 5?+ decay in seconds to minutes at room temperature. Thermal decomposition of 5?+ results in C,N and N,N bond cleavage, yielding 1-norbornyl cation (trapped by solvent) and NO+ (trapped in low yield by the oxidant under chemical oxidation conditions). Two viable mechanisms are presented for 5?+'s thermal decay, both of which invoke nitrosoalkane monomer 5m as an intermediate. In a related study, oxidation of nitrosoalkane 2m is found to mediate its facile denitrosation. This work affords the first examples of electron-transfer-mediated C,N bond cleavage of azodioxides and of nitrosoalkanes. Substantial bond weakening is shown to accompany electron loss from these substrates. For 5, π oxidation leads ultimately to σ C,N bond activation.

Oxidation of Primary Aliphatic Amines to C-Nitroso Dimers

A biphasic system of ethyl acetate or dichloromethane and water containing sodium percarbonate (Na2CO3*3/2H2O2), sodium hydrogen carbonate and N,N,N',N'-tetraacetylethylenediamine oxidizes primary aliphatic amines to aliphatic C-nitroso dimers in most cases in good to excellent yields.