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A series of novel 3-aryl-(3,3-diaryl-3H-naphtho[2,1-b]pyran-8-yl)-3H-naphtho[2,1-b]p y rans has been accessed from 6-bromo-2-naphthol via a four step transformation. Acylation of the dianion derived from the treatment of 6-bromo-2-naphthol with n-butyllithium with Weinreb amides and subsequent reaction with a 1,1,-diarylprop-2-yn-1-ol gave 8-aroyl-3H-naphtho[2,1-b]pyrans in good yield. Addition of lithium trimethylsilylacetylide to the foregoing 8-aroylnaphthopyrans proceeded smoothly with base-mediated desilyation to afford the target bi-naphthopyrans upon acid-catalysed reaction with 2-naphthol. Preliminary evaluation of the photochromic response of the new bi-naphthopyrans revealed reversible independent naphthopyran ring-opening leading to a complex photochromic signature. Novel 6-aroyl-2-naphthols have been used as building blocks to access a series of photochromic bi-naphthopyrans.