Journal Title
Title of Journal: J Chem Crystallogr
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Abbravation: Journal of Chemical Crystallography
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Authors: Sujit Kumar Dehury
Publish Date: 2011/11/26
Volume: 42, Issue: 3, Pages: 214-221
Abstract
2Methyl1phenylvinylcarbamoylphenyl acetate SM empirical formula C18H17NO3 crystallizes in the triclinic space group P−1 with unit cell parameters a = 91087010 Å b = 105694010 Å c = 1613402 Å α = 78059010° β = 89508010° γ = 86683010° Z = 4 The 2methyl1phenylvinylcarbamoylphenyl acetate SM molecule upon irradiation of UVlight below 3000 Å releases acetate group to give six membered cyclic lactam 1 as the major product The quantum yield for the lactam 1 was found to be 0053 An alternate conrotatory 6pi electron photochemically allowed electrocyclic ring closure reaction also occurs upon irradiation to give a sixmembered cyclic zwitterionic intermediate which retains acetate as leaving group A 15H shift would then give the isomerized product 2 The quantum yield for the lactam 2 was found to be 0026 A minor oxidation product lactam 3 that retains the leaving group also formed likely from loss of a proton and tautomerization of enol The loss of one hydrogen molecule is the driving force for revival of aromaticity in the minor product 3 The quantum yield for the lactam 3 was found to be 0012 The low value of total quantum yield 0091 for photocyclization of SM can be explained as the photoproducts absorb light in competition with the photoreactantThe author thanks Dr Mark G Steinmetz for his sincere help and stimulating discussions throughout the project work and Dr Sergey V Lindeman for solving the crystal structure The author would like to thank Marquette University USA for financial support and for the use of research facilities
Keywords:
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