| abstract |
1,204,905. Nitro compounds. TECHNICHEM CO. 3 Oct., 1967 [10 Oct., 1966; 3 Feb., 1967; 15 Aug., 1967], No. 45032/67. Heading C2C. Nitroketones and nitric acid esters are the main products obtained by reaction of an olefinic or cycloolefinic compound in acetic anhydride with nitric acid or acetyl nitrate. When nitric acid is used, its addition to the reaction mixture is so regulated that the formation of an excess of acetyl nitrate during the reaction is avoided. The same condition applies when acetyl nitrate is used as such. Examples are given in which (1) cyclohexen-1-ol acetate yields 2-nitrocyclohexanone, (2) cyclododecen- 1-yl acetate yields 2-nitrocyclododecanone, (3) acetophenone enol acetate yields α-nitroacetophenone, (4) isopropenyl acetate yields nitroacetone, (5) cyclohexene yields 3-nitrocyclohexene, 2-nitrocyclohexyl nitrate and 2-nitrocyclohexyl acetate, (6) cyclopentene yields 3- nitrocyclopentene, 2-nitrocyclopentyl nitrate and 2-nitrocyclopentyl acetate, (7) isobutylene yields α-nitro-tert.-butyl acetate and α-nitrotert.-butyl nitrate, (8) a mixture of 3,3,5- and 3,5,5-trimethyl cyclohexanone enol acetates yields a mixture of 2-nitro-3,3,5-trimethyl- and 2 - nitro - 3,5,5 - trimethyl cyclohexanones and (9) cyclopentanone enol acetate yields 2-nitrocyclopentanone. |