Potassium dinitroethane

Potassium Dinitroethane. See under 1,1-Dinitro-ethane in Vol 6, E164-L... 

Both 1,1-dinitroethane (26) and 1,1-dinitropropane, and their methylol derivatives, 2,2-dinitropropanol (25) and 2,2-dinitro-l-butanol respectively, have been synthesized via the Ter Meer reaction. - The formal and acetal of 2,2-dinitropropanol in the form of a 1 1 eutectic is an energetic plasticizer and so the synthesis of 2,2-dinitropropanol has been the subject of much investigation. On a pilot plant scale 2,2-dinitropropanol (25) is synthesized in 60 % overall yield from nitroethane (22). Thus, treatment of 1 -chloronitroethane (23) with potassium nitrite... 

Phenyltrinitromethanes are similarly obtained from the nitration of gem-nitronitronate salts with a solution of dinitrogen tetroxide in ether. 1,1,1-Trinitroethane (73) can be formed in this way from the potassium salt of 1,1-dinitroethane (24). Nitrolic acids, the products formed... 

Reactions are very dependent on the nature of the base and the reaction conditions used, for example, reaction of 1,1,1-trinitroethane with aqueous potassium hydroxide, or hydroxylamine in methanolic potassium methoxide, gives high yields of potassium 1,1-dinitroethane. ° However, reaction of 1,1,1-trinitroethane with potassium ethoxide, potassium methoxide and ethanolic potassium cyanide is reported to give 2,2-dinitroethylether, methyl-2,2-dinitroethylether and 3,3-dinitropropionitrile respectively, all in approximately 80 % yield via the 1,4-addition of ethoxide, methoxide and cyanide anion to 1,1-dinitroethene respectively. ... 

As discussed above, the nitro groups of tetranitromethane and trinitromethyl compounds are susceptible to nucleophilic attack. Both potassium iodide and alkaline hydrogen peroxide affect the reductive denitration of trinitromethyl groups to em-nitronitronates 1,1,1-trinitroethane (33) is quantitatively reduced to potassium 1,1-dinitroethane (24) on treatment with alkaline hydrogen peroxide. Nucleophiles such as potassium fluoride in DMF can displace nitrite anion from tetranitromethane. Various nucleophiles, including azide, chloride, fluoride and ethoxide have been used to displace one of the nitro groups from fluorotrinitromethane. 

Other early observations of photochromic systems include ter Meer s potassium salt of dinitroethane (9) and Phipson s gate post painted with photochromic lithopone pigment (10). 

Among the substrates were 1-nitropropane, 2-nitrobutane and nitrocyclohexane the less reactive ethyl a-nitrocaproate was also phenylated, at 55°C. 1,1-Dinitroethane and 1,1-dinitropropane in the form of their potassium salts were phenylated in boiling t-butanol (67%) [43],... 

It can be prepd by acidification of potassium-1,1-dinitroethanate,-first prepd in 1876 by Ter Meer (Refs 1 2). In A.D. 

The potassium salts of 1,1-dinitroethane and 1,1-dinitropropane are also phenylated by diphenyliodonium tosylate (25) in rert-butanol under reflux (yields 67-68%). Poor yields were obtained when the reaction was performed in DMF (5%). 4... 

Potassium salts of phenyldinitromethane, 1,1-dinitroethane, and 1,1-dinitropro-pane decompose at 80 °C in DMF and other polar solvents to give nitrile oxides... 

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