Gabbutt, Christopher D., Heron, B. Mark, Kilner, Colin and Kolla, Suresh B. (2012) The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran. Dyes and Pigments, 92 (2). pp. 825-830. ISSN 0143-7208
Abstract

The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling – ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1]benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation – electrocyclisation of the stilbene moiety was detected.

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