Carbenoid induced irreversible ring opening of naphthopyrans

Gabbutt, C. D., Heron, B. M., Thomas, D. A., Light, M. E. and Hursthouse, M. B. (2004) Carbenoid induced irreversible ring opening of naphthopyrans. Tetrahedron Letters, 45, (32), 6151-6154. (doi:10.1016/j.tetlet.2004.06.064).


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Contrary to expectation rhodium carbenoids do not undergo cycloaddition to the 2H-pyran unit of the isomeric naphthopyrans 3 and 5. With 3, a naphtho[2,1-b]pyran-8-ylacetate, 4 is formed and a novel merocyanine dye 6 results from a cycloaddition across the C-5-C-6 double bond of the naphtho[1,2-b]pyran 5. Tethering the carbenoid to the naphtho[1,2-b]pyran system 5, as in 10, results in a similar mode of addition and affords the intensely coloured tetracycle 11.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/j.tetlet.2004.06.064
Related URLs:
Keywords: photochromic properties, chemoselectivity, transformations, chloride, pyrans
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 20203
Accepted Date and Publication Date:
2 August 2004Published
Date Deposited: 20 Feb 2006
Last Modified: 31 Mar 2016 11:37

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