548796-75-4Relevant academic research and scientific papers
Observations on the synthesis of photochromic naphthopyrans
Gabbutt, Christopher D.,Heron, B. Mark,Instone, Alicia C.,Thomas, David A.,Partington, Steven M.,Hursthouse, Michael B.,Gelbrich, Thomas
, p. 1220 - 1230 (2003)
1-Naphthol reacts with 1,1-diarylprop-2-yn-1-ols 5a,b, under alumina catalysis, by two pathways to give the photochromic naphtho[1,2-b]pyrans 6a,b, together with the propenylidenenaphthalenones 7a,b, representatives of a new class of merocyanine dyes. With 2-methyl-1-naphthol, formation of the photochrome is suppressed; the only products are merocyanines 7c,d. The cyclocondensation of 2-naphthol with 5a,b proceeds much more efficiently, to give the naphtho[2,1-b]pyrans 14a,b. Pyran formation is not suppressed from either 1-bromo- or 1-(4 -methoxyphenyl)-2-naphthol; reaction with 5a,b merely results in expulsion of the C-1 substituent. An alternative pathway supervenes in the reaction of 1-methyl-2-naphthol with 5a to give the benz[e]indanone 17, the constitution of which was determined by X-ray crystallography. Reaction of the 1,3,3-triarylpropynols 19a,b with 1-naphthol affords the naphthopyrans 20 together with merocyanines 21, whilst the isomeric pyrans 23 are efficiently produced from 2-naphthol. The configuration of merocyanines 7a and 21a was unequivocally established by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
2,2,4,6-Tetraaryl-2H-benzo[h]chromenes: The influence of electronic communication between aryl substituents on their photochromism
Aiken, Stuart,Armitage, Georgina K.,Crossley, Daniel L.,Dobson, Rhianne,Gabbutt, Christopher D.,Heron, B. Mark,Jacquemin, Denis,Rice, Craig R.,Soltowska, Nicola,de Azevedo, Orlando D. C. C.
, (2022/01/03)
A series of photochromic 2,2,4,6-tetraaryl-2H-benzo[h]chromenes have been efficiently synthesised by two complementary strategies employing the condensation of 1,1,3-triarylprop-2-yn-1-ols with 4-substituted 1-naphthols and Suzuki cross-coupling chemistry
The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans
Gabbutt, Christopher D.,Heron, B. Mark,Kilner, Colin,Kolla, Suresh B.
experimental part, p. 4874 - 4883 (2010/11/19)
1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochrom
