Novel photoreactions of 2-aza-1, 4-dienes in the triplet excited state and via radical-cation intermediates. 2-Aza-di-π-methane rearrangements yielding …

…, AR Agarrabeitia, M Martin-Fontecha…

Index: Armesto, Diego; Caballero, Olga; Ortiz, Maria J.; Agarrabeitia, Antonia R.; Martin-Fontecha, Mar; Torres, M. Rosario Journal of Organic Chemistry, 2003 , vol. 68, # 17 p. 6661 - 6671

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Citation Number: 17

Abstract

Triplet-sensitized irradiation of 2-aza-1, 4-dienes affords N-cyclopropylimines via 2-aza-di-π- methane (2-ADPM) rearrangement pathways. In the case of the pentaphenyl-substituted azadiene 1, irradiation leads to formation of cyclopropylimine 2 as well as N-vinylaziridine 3. The transformations represent the first examples of di-π-methane rearrangement reactions that yield three-membered heterocyclic products. SET-sensitized irradiation of 2-aza-1, 4- ...

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