Easy access to medium rings by entropy/strain reduction,Part 3. Competition between dihydroazepine and enamine formation in reaction of tetrahalosubstituted dibromides with primary amines |
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Authors: | James G Walsh Declan G Gilheany |
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Abstract: | The reaction of Z,Z‐2,3,4,5‐tetrahalo‐2,4‐dien‐1,6‐dibromides ( 3 , R1 ‐ R4 = Cl, Br) with primary amines in the presence of potassium carbonate leads to both the dihydroazepines 4 and secondary enamines 5 . The formation of enamine is suppressed with toluene sulfonamide as nitrogen source. (2Z,4Z)‐2,3,4,5‐Tetrabromo‐hexa‐2,4‐diene‐1,6‐diol (2, R1 ‐ R4 = Br) is atropisomeric in solution. |
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