Thermal isomerization of aminomethyl- or oxygen-bridged biphenyl systems possessing dicyanovinyl and sec-amino groups in ortho- and ortho0-positions was investigated. Both systems underwent cyclization via tert-amino effect. Thus, 2-(2-{[2-(sec-amino)benzyl]-N-methylamino}benzylidene)malononitriles gave tetrahydroquinolines, whereas a 2-[2-(sec-amino)phenoxy]benzylidenemalononitrile isomerized to dibenzoxazonine derivative. The ring closure reaction was studied by differential scanning calorimetry measurements.
Study on the scope of tert-amino effect: new extensions of type 2 reactions to bridged biaryls
SCHLICH, MICHELE;
2012-01-01
Abstract
Thermal isomerization of aminomethyl- or oxygen-bridged biphenyl systems possessing dicyanovinyl and sec-amino groups in ortho- and ortho0-positions was investigated. Both systems underwent cyclization via tert-amino effect. Thus, 2-(2-{[2-(sec-amino)benzyl]-N-methylamino}benzylidene)malononitriles gave tetrahydroquinolines, whereas a 2-[2-(sec-amino)phenoxy]benzylidenemalononitrile isomerized to dibenzoxazonine derivative. The ring closure reaction was studied by differential scanning calorimetry measurements.
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