Photochemical & Photobiological Sciences 2010-08-01

Paternò-Büchi reaction between furan and heterocyclic aldehydes: oxetane formation vs. metathesis.

Maurizio D'Auria, Rocco Racioppi, Licia Viggiani

Index: Photochem. Photobiol. Sci. 9(8) , 1134-8, (2010)

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Abstract

The photochemical reaction of 2-substituted heterocyclic aldehydes with furan gave the corresponding exo oxetane derivatives through the excited triplet state. However, in situ the oxetane derivatives were converted through a metathesis reaction into the corresponding Z,E-butadienyl formate derivatives. On the contrary, 3-substituted heterocyclic aldehydes gave the corresponding exo oxetane derivatives. The effect of 2-substituted heterocyclic ring in order to facilitate the metathesis reaction is explained considering the possible participation of the pi aromatic orbitals in the oxetane C-O bond cleavage.