Helvetica chimica acta

Synthesis of Benzo [g] isochromenes through Photo??Dehydro??Diels–Alder Reaction

P Wessig, G Müller, R Herre, A Kühn

Index: Wessig, Pablo; Mueller, Gunnar; Herre, Robert; Kuehn, Andreas Helvetica Chimica Acta, 2006 , vol. 89, # 11 p. 2694 - 2719

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Citation Number: 18

Abstract

Abstract The Photo-Dehydro-Diels–Alder (PDDA) reaction is shown to be a versatile method for the preparation of highly functionalized naphthalenes. Thus, ketones 1 could be cyclized to the 1H-benzo [g] isochromen-4-(3H)-ones 11 and 12, mostly in good yields. The influence of various substituents on the regioselectivity of the reaction was investigated, and the mechanism is discussed based on theoretical calculations.