Tetrahedron letters

Intramolecular formal [4+ 2] cycloaddition reactions of secondary and tertiary aryldiacetylene alcohols

D Rodrı́guez, D Quintás, A Garcı́a, C Saá…

Index: Rodriguez, David; Quintas, Domingo; Garcia, Alberto; Saa, Carlos; Dominguez, Domingo Tetrahedron Letters, 2004 , vol. 45, # 24 p. 4711 - 4714

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Citation Number: 10

Abstract

Thermal and thionyl chloride induced cycloaromatizations of secondary and tertiary aryldiacetylene alcohols were studied. The secondary alcohol did not respond to thionyl chloride, but in all the other cases presumptive biradical intermediates evolved either by intramolecular radical coupling or, when derived from a xanthene scaffold, by intramolecular radical acylation to a diketone that finally afforded a p-methylene-quinone.