Alkynes nitric oxide

Busker, E. Budzikiewicz, H. Studies in CI-MS. 2. Isobutane and Nitric Oxide Spectra of Alkynes. Org. Mass Spectrom. 1979,14, 222-226. 

Alkanes n-butene, isopentane, isooctane Cydoalkanes t dohezane, methylcyclopentane Olefins (sometimes called alkenes ) ethylene, propylene, butene Cydoolefins ( clohezene Alkynes acetylene Aromatics toluene, i ene CHLORINATED HYDROCARBONS ALDEHYDES, RCHO formaldehyde, acetaldehyde KETONES, RCX R " acetone, methylethylketone NITRIC OXIDE, NO ... 

Reactions of M4 OR)u with Carbon Monoxide, Isocyanides, Nitriles, Nitric Oxide, and Alkynes... 

Very interesting transformations were reported in terminal alkynes RC=CH (R = alkyl, aryl, alkoxy, carboxylate, etc.). They react readily with nitric acid, in aqueous nitromethane (1 1) and in the presence of catalytic amounts of tetra-butylammonium tetrachloroaurate to give 3,5-disubstituted isoxazoles 15 in 35% to 50% isolable yield (92). The reaction might proceed via a nitrile oxide intermediate by attack of an electrophile (AuCh or H+) and of a nucleophile (N02 ) on the triple bond to form a vinyl nitrite, which is converted to a nitrile oxide by the action of gold(III) or of nitric acid (Scheme 1.8). 

Air, copper, halogens (chlorine, bromine, iodine), alkali metals Acids, water, hydroxy compounds, polychlorinated hydrocarbons (for example, CCI, halogens, carbon dioxide, oxidants, terminal alkynes Halogens (bromine, chlorine. Iodine), hydrofluoric acid, liquid oxygen, calcium or sodium hypochlorite, heavy metals (silver, gold, mercury), nitric acid... 

The oxidation of alkynes mostly leads to 1,2-diketones. This can be accomplished under various reaction conditions as summarized in a recent review. Typical oxygen donors are nitric acid, dimethylsulfoxide and water. In addition, alkynes might also give rise to esters or fiirans. 

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