THE CHEMISTRY OF FULMINIC ACID REVISED

Article abstract of DOI:10.1016/S0040-4020(01)96763-8

The availability of a new synthesis of fulminic acid by hydrolysis of trimethylsilanecarbonitrile oxide allowed a reinvestigation of the chemistry of the title compound.Thus, cycloadditions to olefinic and acetylenic dipolarophiles are improved with respect to previous results and the oligomerisation is proved to occur via the reactive species hydroxyiminoacetonitrile oxide 7 and hydroxyiminomethyl-hydroxyimino-acetonitrile oxide 8.The Z-configuration, found for the oxime groups in these intermediates, is maintained in their derivatives, under kinetic control.