Tetrahedron p. 4113 - 4118 (1987)
Update date:2022-08-03
Topics:
Brehme, Rainer
Klemann, Anke
Sulfonyl isocyanates attack the arylaldehyde N,N-dialkylhydrazones 1-3 at the nitrogen or carbon of the azomethine function leading to the formation of the hexahydro-1,3,5-triazine-2,4-diones 4-6 or arylglyoxylic acid sulfonamide-N,N-dialkylhydrazones 7-9 (scheme 1).Under equal experimental conditions the position of the electrophilic attack depends on the contribution of the dipolar structures I'<-->I'' determined by the electron withdrawing or donating potential of the substituents R1 and NR2.The normal reactivity of the =C=N-function is described by eq.1, the umpolung by eq.2.These different reactions correspond to the 13C-chemical shifts of the azomethine carbon atoms.
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(1987)