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A solid S-methyl derivative (methyl 2-cyano-3- hydroxythiocrotonimidate) of the enol structure of Ⅳ was obtained by treating Ⅱwith methyl iodide in 4% sodium hydroxide solution. The ethyl group of Ⅱ was lost during this alkylation reaction. Upon mild oxidation of Ⅸwith iodine in potassium iodide, a disulfide, which was characterized as 3,3'-dithiobis [2- (l-hydroxyethylidene)-3-imino propionitrile](ⅩⅣ), was formed. It was surprising to find that if Ⅱ was mildly oxidized in the same manner with iodine in potassium iodide the ethyl group was lost and the same product was formed. The absence of hydrogen iodide salt formation was demonstrated by a negative halogen analysis. |
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