Photochemistry of conjugated nitrogen – carbonyl systems, 6. Photodimerization of 2,4‐dioxotetrahydropyridines

Sato, Eisuke F.; Todoriki, Reiko; Kanaoka, Yuichi; Flippen, J. L.; Karle, Isabella L.; Witkop, Bernhard

doi:10.1002/jlac.198819881008

Cited by 4 publications

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“…In contrast, vinylogous imides, e.g. 5 [14] or 6a [ 151, the vinylogous N-acylcarbamate 6b [16], and pyrimidinediones as uracil [ 171 photodimerize and undergo [2 + 21 cycloadditions to alkenes, mostly in acetone-sensitized reactions. We now report on the synthesis of the five-membered 3-oxopyrrole-1 -carboxylate 7a and on comparative results of its photochemical behaviour to that of furanone la and thiophenone lb.…”

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Photochemistry of ethyl 2,3‐dihydro‐2,2‐dimethyl‐3‐oxo‐1H‐pyrrole‐1‐carboxylate

Patjens¹,

Margaretha²

1989

Helvetica Chimica Acta

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Dedicated to Prof. Dr. W. Walter on the occasion of his 70th birthday (1 5.1X. 89) The title compound 7 is obtained by reductive dehalogenation from 4-bromo-2,3-dihydro-2,2,-dimethyl-3-0x0-1H-pyrrole-1-carboxylate (8) in 90% yield. Aza-enone 7 undergoes [2 + 21 cycloaddition from the triplet state with both electron-rich and electron-deficient alkenes. The behaviour of 7 in light-induced reactions is compared to those of 2,2-dimethyl-3(2H)-furanone (la) and of the corresponding thiophenone lb. In the photodimerization and the cycloaddition to either 2,3-dimethylbut-2-ene or to dimethyl maleate of these ketonic five-membered heterocycles with one heteroatom, the overall efficiency increases in going from the furan l a to the thiophene l b and to the pyrrole 7.

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confidence: 99%