The development of a new method for the trapping of nitric oxide

Substituted butadienes (1) and (2) were synthesised and their salts prepared, (3) and (4). Compounds (1), (3) and (4) were reacted with nitric oxide (NO); causing the salts to form a material insoluble in deuterated chloroform, and the free amine to undergo an unidentified process after a long reaction time. (Fig. 3517A).;Phenyl cyclopropane (5) reacted with NO to give 5-phenyl-4, 5-dihydroisoxazole (6). (Fig. 3517B).;Similarly, racemic trans-1, 2-diphenylcyclopropane (7) reacted with NO to give 3,5-diphenyl-4, 5-dihydroisoxazole (8). (Fig. 3517C).;Racemic trans-cyclopropane esters (9) and (10) were reacted in a similar way to give the 4,5-dihydroisoxazoles (11) and (12). (Fig. 3517D).;Epoxides (13) and (14) reacted with NO to give the nitrate esters (15) and (16). The X-ray structure of (15a) was obtained. (Fig. 3517E).;Epoxides (13) reacted with HNO3 to give the nitrate (15), providing evidence supporting the suggestion that the reaction with NO proceeds via formation of HNO3 in solution.