Journal of the Chemical Society. Perkin transactions I p. 1631 - 1636 (1988)
Update date:2022-09-26
Topics: Transformations Acid-promoted
Barluenga, Jose
Bayon, Ana M.
Campos, Pedro
Asensio, Gregorio
Gonzalez-Nunez, Elena
Molina, Yolanda
A general method for the synthesis of N, O-aminals derived from primary aromatic amines is described.The reactivity of these compounds under neutral and acidic conditions has been studied and the title compounds can be envisaged as general purpose H2C=NAr or (H2C=NAr)+ equivalents.N,O-Aminals have been converted into perhydrotriazines by moderate heating and into bis(4-aminoaryl)methane derivatives or N-benzylarylamines, respectively, when heated in acidid media with pH control.Reduction od N,O-acetals with sodium cyanoborohydride has revealed that the C-O bond is broken exclusively in acidic media.
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