Carbenoid induced irreversible ring opening of naphthopyrans

Christopher D. Gabbutt, B. Mark Heron, David A. Thomas, Mark E. Light, Michael B. Hursthouse

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6151-6154
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number32
Early online date6 Jul 2004
DOIs
Publication statusPublished - 2 Aug 2004
Externally publishedYes

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