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SYNTHESIS OF AMIDRAZONIUM SALTS BY THE REACTION OF S-METHYLTHIOAMIDIUM IODIDES WITH HYDRAZINES
Zelenin, K. N.,Pinson, V. V.,Khrustalev, V. A.
, p. 1410 - 1415 (2007/10/02)
A series of amidrazonium iodides with various degrees of substitution and relative positions for the substituents were obtained by the reaction of S-methylthioamidium iodides with hydrazines.The effect of the structure of the thioamide and hydrazine components and also of temperature on the direction of the reaction was studied.For methylhydrazine preferential reaction at the N1 atom is observed.Increase in the volume and electron-withdrawing characteristics of the substituent in the hydrazine determines attack at the unsubstituted nitrogen atom.The amidrazonium iodides, which have as it were one hydrogen atom at the N3 atom, exist in the configuration with the syn arrangement of the first and third nitrogen atoms, stabilized by an intramolecular hydrogen bond.The 3,3-disubstituted amidrazonium iodides exist in the E configuration.
