Nitroalkanes, prim

A mixture containing valeroyl nitrate, prepared at ca. 20° from excess valeroyl anhydride and 90%-HNOg, dropped through a glass tube packed with glass helices and heated to ca. 290° 1-nitrobutane. Y 56.5%. Prim., sec., tert., as well as ar. nitro compds. can be prepared by this method without isomerization. This makes decarboxylative nitration the most broadly applicable and for many nitroalkanes the best of the known syntheses. F. e. s. G. B. Bachman and T. F. Biermann, J. Org. Chem. 55, 4229 (1970). 

The importance of nitroalkanes as building blocks and precursors of prim-amines and ketones is exemplified. 

Use of p-toluidine gives good yields of compounds suitable for the identification and characterization of nitroalkancs. E., also formation of nitrohexa-hydropyrimidines (s. Synth. Meth. 3, 314) from prim, nitroalkanes, s. M. B. Winstead, R. G. Strachan, and H. W. Heine, J. Org. Chem. 26, 4116 (1961). 

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