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A simple and general synthesis of symmetrical and unsymmetrical bis(arylamino)methanes. Reactions of N,O‐acetals with nitrogen bases
Author(s) -
Barluenga José,
Bayón Ana M.,
Campos Pedro J.,
Canal Gonzalo,
Asensio Gregorio,
GonzálezNuñez Elena,
Molina Yolanda
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881211019
Subject(s) - chemistry , acetal , decomposition , base (topology) , amine gas treating , phenyllithium , nitrogen , lithium (medication) , simple (philosophy) , medicinal chemistry , organic chemistry , medicine , mathematical analysis , mathematics , endocrinology , philosophy , epistemology
Bis(arylamino)methanes 4 free of amine contamination have been efficiently synthesized from N,O‐acetals 1 following three different methodologies. The first two are useful for symmetrical aminals and involve the decomposition of an N,O‐acetal by a base (phenyllithium or a lithium arylamide) and trapping of the resulting methyleneamine 2 by the equimolar amount of the corresponding arylamine. The third method allows the preparation of either symmetrical or unsymmetrical aminals and consists of decomposing the starting N,O‐acetal 1 by heating in vacuo in the presence of the desired arylamine.