1. Experimental and Theoretical Studies on the Radical-Cation-Mediated Imino-Diels–Alder Reaction
- Author
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M. Consuelo Jiménez, Miguel A. Miranda, Luis R. Domingo, and Raúl Pérez-Ruiz
- Subjects
Pyrylium salt ,Photochemistry ,Biochemistry ,Catalysis ,Photoinduced electron transfer ,chemistry.chemical_compound ,Electron transfer ,QUIMICA ORGANICA ,Mechanisms ,Facile synthesis ,Photosensitizer ,4+2 cycloaddition ,Physical and Theoretical Chemistry ,Diels–Alder reaction ,Organic Chemistry ,Transition state ,N-Arylimines ,chemistry ,Radical ion ,Tetrahydroquinoline derivatives ,Thiobenzophenone ,2,4,6-triphenylpyrylium salt ,Photoinduced electron-transfer ,Flash photolysis ,martinellic acid - Abstract
[EN] The feasibility of an electron transfer imino-Diels Alder reaction betweenN-benzylideneaniline and arylalkenes in the presence of a pyrylium salt as a photosensitizer has been demonstrated by a combination of product studies, laser flash photolysis (LFP), and DFT theoretical calculations. A stepwise mechanism involving two intermediates and two transition states is proposed., Financial support from the MICINN (Grants CTQ2010-14882, CTQ2009-13699, CTQ2009-11027, and JCI-2010-06204) and from the UPV (Grant No. 20100994 and MCI Program) is gratefully acknowledged. Dedicated to Prof. Dr. Jaime Primo (Universidad Politecnica de Valencia) on the occasion of his 60th birthday.
- Published
- 2011