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.

LanguageEnglish
Pages6151-6154
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number32
Early online date6 Jul 2004
DOIs
Publication statusPublished - 2 Aug 2004
Externally publishedYes

Fingerprint

Cycloaddition
Cycloaddition Reaction
Pyrans
Rhodium
naphtho(2,1-b)pyran
merocyanine dye

Cite this

Gabbutt, Christopher D. ; Heron, B. Mark ; Thomas, David A. ; Light, Mark E. ; Hursthouse, Michael B. / Carbenoid induced irreversible ring opening of naphthopyrans. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 32. pp. 6151-6154.
@article{972ece1bc2ed4b22a1d09e15c5fc836d,
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 = "8",
day = "2",
doi = "10.1016/j.tetlet.2004.06.064",
language = "English",
volume = "45",
pages = "6151--6154",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "32",

}

Carbenoid induced irreversible ring opening of naphthopyrans. / Gabbutt, Christopher D.; Heron, B. Mark; Thomas, David A.; Light, Mark E.; Hursthouse, Michael B.

In: Tetrahedron Letters, Vol. 45, No. 32, 02.08.2004, p. 6151-6154.

Research output: Contribution to journalArticle

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=3142730460&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.06.064

DO - 10.1016/j.tetlet.2004.06.064

M3 - Article

VL - 45

SP - 6151

EP - 6154

JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 32

ER -