Two Alternative Pathways for the Interaction of Hexacyanocyclopropane with Nucleophiles

Methanol molecules add to the cyano groups of hexacyanocyclopropane 1 in the presence of sodium methylate to give 1,4-adduct 2. The interaction of 1 with N-methylpyridinium iodide leads to opening of the cyclopropane ring and to the formation of propenide 3 and iodine cyanide 4; the structure of 2 was established by an X-ray crystallographic study.