Date of Award
Union College Only
Bachelor of Science
In 1939 Seigle and Hass were successful in preparing numerous dinitro paraffins such as 2, 3-dimethyl-2, 3-dinitro butane and 2, 3-dimethyl-2, 3-dinitro pentane by the reaction of salts of nitroparaffins with halonitroparaffins. They were unable to do so however, in the cases where primary nitro compounds were involved. More recently, in an unpublished work Sottysiak believed that he prepared the 2, 3-dimethyl-2, 3-dinitro butane by a Wurtz reaction in liquid ammonia, in which 2-nitro-2-chloro propane was reduced by sodium. Because of the strong reducing properties of a solution of sodium in anhydrous liquid ammonia, it was hoped that the 3, 4-dinitro hexane could be prepared in this manner. Sodium, when added to the nitro alkanes evolves hydrogen to form the sodium salt of the pseudo acid. A similar reaction was expected when the chloro-nitro propane was added to the liquid ammonia, but this should not affect the Wurtz reaction.
Gilmore, James S., "The reactions of l-chloro-l-nitro propane in anhydrous liquid ammonia" (1943). Honors Theses. 1850.