Abstract
N-methyl-N-(1-phenylvinyl)benzamide (I) has empirical formula C16H15NO, crystallizes in the monoclinic space group, P21/n, with unit cell parameters a = 8.9101(2) A ˚ , b = 15.1416(4) A ˚ , c = 9.7737(2) A ˚ , a = 90, b = 109.3320(10), c = 90, Z = 4. Interestingly, the Compound (I) undergoes photocyclization upon irradiation of light to give two cyclic lactams (A and B) below 3100 A ˚ . Compound (I) can be cyclized at either of two equivalent ortho positions. The mechanism for formation of lactam A may involve electrocyclic ring closure reaction upon irradiation of light to give six-membered cyclic zwitterionic intermediate. The ring proton rearranges via (1, 5)-H shift to give isomerized product A. The minor photoproduct B is supposed to be formed via photocyclization process fol- lowed by a loss of proton and the tautomerized product undergoes oxidation for the revival of aromaticity.
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