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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Official URL: http://dx.doi.org/10.1016/j.tetlet.2004.06.064
Description/Abstract
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 |
|---|---|
| Uncontrolled Keywords: | photochromic properties, chemoselectivity, transformations, chloride, pyrans |
| Related URLs: | http://dx.doi.org/10.1016/j.te...004.06.064 |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 20203 |
| URI: | http://eprints.soton.ac.uk/id/eprint/20203 |
| Deposited On: | 20 Feb 2006 |
| Last Modified: | 01 Jun 2011 17:10 |
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