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Photoinduced Addition of Phthalimide to Unactivated Alkynes


  • This paper is part of a special issue dedicated to Professor J. C. (Tito) Scaiano on the occasion of his 60th birthday.


Photoexcited phthalimide in equilibrium with its conjugated base produces the regioselective hydrophthalimidation of conjugated alkynes. The vinylphthalimide thus obtained is hydrolyzed to the corresponding carbonyl compound. With unconjugated alkynes, the outcome is a double addition of phthalimide to the triple bond. The reaction is assumed to take place via single electron transfer from either the alkyne or the phthalimide anion to the excited phthalimide as the primary photoprocess.

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