Potassium Cyanide Links

Action of Alkyl Halides and Silver Cyanide.—The compounds formed by the reaction of alkyl halides with metal cyanides exhibit a new and peculiar case of somerism. When silver cyanide, instead of potassium cyanide, acts upon an alkyl halide there is formed a compound of the same composition as methyl cyanide, viz., C2H3N, but with distinctly different properties, i.e.y an isomeric compound. It is known therefore as methyl iso-cyanide. The explanation of the isomerism of these two compounds is furnished by the character of the products which they yield when decomposed with water. We have proven that in methyl cyanide the methyl carbon atom is linked to the cyanogen carbon atom. 

It would seem therefore that the only problem would be to determine whether they exist in the form of alkyl cyanides, i.e., with the hydrogen, potassium or silver linked to the carbon atom of the cyanogen or whether they are in the form of the alkyl isocyanides with the nitrogen atom of the cyanogen group linked to the other element. This, however, is where the facts become perplexing. 

By oxidation of ( )-magnocurarine iodide with potassium ferri-cyanide in aqueous sodium carbonate at room temperature, a crystalline O,0-dehydromagnoeurarine is obtained (iodide, rnp 225°-227°) to which the bisbenzyltetrahydroisoquinoline structure XXI was assigned (51). In this way, through a chemical reaction, two types of bases considered biogcnetically related were linked. 

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