Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)

Simon B. Bedford; Michael J. Begley; Philip Cornwall; Joel P. Foreman; David W. Knight

doi:10.1039/P19960002827

Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)

Simon B. Bedford, Michael J. Begley, Philip Cornwall, Joel P. Foreman, David W. Knight

Western Sydney University

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The Ito-Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding silyl acetate 17b in solution at -4Â°C. The intermediate reacts efficiently with a range of reactive Diels-Alder dienophiles with moderate to good levels of regioselection; the structure of the major diastereoisomer has been determined by X-ray analysis.

Original language	English
Pages (from-to)	2827-2832
Number of pages	6
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	23
DOIs	https://doi.org/10.1039/P19960002827
Publication status	Published - 1996

Keywords

chemistry

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10.1039/P19960002827

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title = "Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)",

abstract = "The Ito-Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding silyl acetate 17b in solution at -4{\^A}°C. The intermediate reacts efficiently with a range of reactive Diels-Alder dienophiles with moderate to good levels of regioselection; the structure of the major diastereoisomer has been determined by X-ray analysis.",

keywords = "chemistry",

author = "Bedford, {Simon B.} and Begley, {Michael J.} and Philip Cornwall and Foreman, {Joel P.} and Knight, {David W.}",

year = "1996",

doi = "10.1039/P19960002827",

language = "English",

volume = "23",

pages = "2827--2832",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

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publisher = "Royal Society of Chemistry",

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T1 - Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)

AU - Bedford, Simon B.

AU - Begley, Michael J.

AU - Cornwall, Philip

AU - Foreman, Joel P.

AU - Knight, David W.

PY - 1996

Y1 - 1996

N2 - The Ito-Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding silyl acetate 17b in solution at -4Â°C. The intermediate reacts efficiently with a range of reactive Diels-Alder dienophiles with moderate to good levels of regioselection; the structure of the major diastereoisomer has been determined by X-ray analysis.

AB - The Ito-Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding silyl acetate 17b in solution at -4Â°C. The intermediate reacts efficiently with a range of reactive Diels-Alder dienophiles with moderate to good levels of regioselection; the structure of the major diastereoisomer has been determined by X-ray analysis.

KW - chemistry

UR - http://handle.westernsydney.edu.au:8081/1959.7/uws:47683

U2 - 10.1039/P19960002827

DO - 10.1039/P19960002827

M3 - Article

SN - 0300-922X

VL - 23

SP - 2827

EP - 2832

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

ER -

Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)

Abstract

Keywords

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