Carbenoid induced irreversible ring opening of naphthopyrans

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

doi:10.1016/j.tetlet.2004.06.064

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 journal › Article › peer-review

12 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 language	English
Pages (from-to)	6151-6154
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	32
Early online date	6 Jul 2004
DOIs	https://doi.org/10.1016/j.tetlet.2004.06.064
Publication status	Published - 2 Aug 2004
Externally published	Yes

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title = "Carbenoid induced irreversible ring opening of naphthopyrans",

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.",

author = "Gabbutt, \{Christopher D.\} and Heron, \{B. Mark\} and Thomas, \{David A.\} and Light, \{Mark E.\} and Hursthouse, \{Michael B.\}",

year = "2004",

month = aug,

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doi = "10.1016/j.tetlet.2004.06.064",

language = "English",

volume = "45",

pages = "6151--6154",

journal = "Tetrahedron Letters",

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T1 - Carbenoid induced irreversible ring opening of naphthopyrans

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Thomas, David A.

AU - Light, Mark E.

AU - Hursthouse, Michael B.

PY - 2004/8/2

Y1 - 2004/8/2

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/3142730460

U2 - 10.1016/j.tetlet.2004.06.064

DO - 10.1016/j.tetlet.2004.06.064

M3 - Article

AN - SCOPUS:3142730460

SN - 0040-4039

VL - 45

SP - 6151

EP - 6154

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Carbenoid induced irreversible ring opening of naphthopyrans

Abstract

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