Unexpected formation of new photochromic compounds derived from 3,3-diphenyl-3H-naphtho[2,1-b]pyran-1-one

Two new unexpected photochromic compounds were obtained from naphtho[2,1-b]pyran-1-one 1. The reaction of this ketone with the silyl enol ether methyl trimethylsilyl dimethylketene acetal, catalyzed by TiCl4, afforded the photochromic dihydronaphtho[2,1-b]pyranone 2. The Reformatsky reaction of ketone 1 with ethyl bromoacetate led to the formation of the expected alcohol that under acid treatment gave, unexpectedly, the novel photochromic benzocoumarin 6. UV irradiation compounds 2 and 6 in solution provided thermally stable photoproducts that returned to the initial uncoloured forms under visible irradiation. The photochromic behaviour of these compounds and the structures of the photoproducts formed in these reactions were characterized by 1D and 2D NMR.

Figure optionsDownload as PowerPoint slide