The University of Southampton
University of Southampton Institutional Repository

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


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.

Full text not available from this repository.

More information

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


Local EPrints ID: 20203
ISSN: 0040-4039
PURE UUID: 2e1c16b7-b74d-49e3-ae74-59d26b4d566d
ORCID for M. E. Light: ORCID iD

Catalogue record

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

Export record



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

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton:

ePrints Soton supports OAI 2.0 with a base URL of

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.