Carbenoid induced irreversible ring opening of naphthopyrans
Carbenoid induced irreversible ring opening of naphthopyrans
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.
photochromic properties, chemoselectivity, transformations, chloride, pyrans
6151-6154
Gabbutt, C. D.
94192b7e-b99b-4611-943e-fe645f2d6a52
Heron, B. M.
64aef16b-7be8-40ee-980c-74f4169f8057
Thomas, D. A.
b81b28b6-1c3d-4527-89df-e57b347f22dc
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
2 August 2004
Gabbutt, C. D.
94192b7e-b99b-4611-943e-fe645f2d6a52
Heron, B. M.
64aef16b-7be8-40ee-980c-74f4169f8057
Thomas, D. A.
b81b28b6-1c3d-4527-89df-e57b347f22dc
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
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), .
(doi:10.1016/j.tetlet.2004.06.064).
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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Published date: 2 August 2004
Keywords:
photochromic properties, chemoselectivity, transformations, chloride, pyrans
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Local EPrints ID: 20203
URI: http://eprints.soton.ac.uk/id/eprint/20203
ISSN: 0040-4039
PURE UUID: 2e1c16b7-b74d-49e3-ae74-59d26b4d566d
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Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 03:04
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Author:
C. D. Gabbutt
Author:
B. M. Heron
Author:
D. A. Thomas
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