Abstract
Restricted rotation about the C(1)-N single bond in N, N-disubstituted 1-aminoanthracenes has been investigated. The synthesis, isolation and characterization of diastereomers arising out of the hindered rotation about the $$\hbox {C}_{\mathrm{SP}^{2}}\hbox {-N}_{\mathrm{SP}^{2}}$$ single bond has been demonstrated. With unsymmetrical substituents on the Nitrogen atom, preferred conformations about the C(1)-N bond were observed. SYNOPSIS Restricted rotation about the C(1)-N single bond in N, N-disubstituted-1-aminoanthracenes has been investigated. Diels-Alder reaction of N, N-disubstituted-1-aminoanthracenes with dimethylacetylenedicarboxylate results in the restricted rotation of the aryl C(1)-N bond. The introduction of the C(9)-C(10) bridge gives rise to atropisomers when the substituents at C(1)-N position are non-equivalent.
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