Tetrahedron

Photochemistry of 7-acetoxybenzopyran derivatives. Synthesis of eupatoriochromene and encecalin

MA Miranda, J Primo, R Tormos

Index: Miranda, Miguel A.; Primo, Jaime; Tormos, Rosa Tetrahedron, 1989 , vol. 45, # 23 p. 7593 - 7600

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Citation Number: 7

Abstract

The photolysis of the 7-acetoxybenzopyran derivatives 1a-5a has been carried out. Chromene 1a was found to undergo extensive photopolymerization. Chromanone 2a underwent a rather inefficient photo-Fries rearrangement to the 6-and 8-acetyl derivatives 2b and 2c. Diacetoxychromene 3a gave the unsaturated ketone 8 as the main product, besides its deacetylation analogue 9 and chromanone 11. Diacetoxychroman 4a afforded a ...