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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), pp. 6151-6154. (doi:10.1016/j.tetlet.2004.06.064).

Record type: Article

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.

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More information

Published date: 2 August 2004
Keywords: photochromic properties, chemoselectivity, transformations, chloride, pyrans

Identifiers

Local EPrints ID: 20203
URI: http://eprints.soton.ac.uk/id/eprint/20203
ISSN: 0040-4039
PURE UUID: 2e1c16b7-b74d-49e3-ae74-59d26b4d566d
ORCID for M. E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 17 Jul 2017 16:29

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Contributors

Author: C. D. Gabbutt
Author: B. M. Heron
Author: D. A. Thomas
Author: M. E. Light ORCID iD

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