Action of sodium in liquid ammonia on 6-(methylthio)-m-tolualdehyde diethyl acetal

Autor: Gol'dfarb, Ya. L., Skorova, A. É., Kirmalova, M. L.
Zdroj: Russian Chemical Bulletin; August 1966, Vol. 15 Issue: 8 p1365-1370, 6p
Abstrakt: Conclusions 1.In the reaction of 6-(methylthio)-m-tolualdehyde diethyl acetal with six equivalents of sodium in liquid ammonia 2,4-xylenethiol is formed, and in the reaction with two equivalents of sodium 6-mercapto-m-tolualdehyde diethyl acetal is formed and may be identified in the form of the mercury thiolate.2.When treated with alcoholic solutions of ammonia or amines the product formed on neutralization of an alkaline solution of the mercapto acetal is converted into a nitrogeneous compound which can be assigned the structure of 2,8-dimetiiyl-6H,12H-dibenzo[b,f][1,5]dithiocin-6,12-imine or its N-derivatives, respectively.3.The formation of nitrogenous compounds of different types in the transformations of 6-(methylthio)-m-tolualdehyde and 5-alkyl-2-(alkylthio)-3-thiophenecarboxaldehyde acetals is probably associated with the difference in geometry between the benzene and thiophene rings.
Databáze: Supplemental Index