A brief and mild method for the generation of Benzofuran-2,3-xylylene in solution

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

doi:10.1055/s-1991-20819

A brief and mild method for the generation of Benzofuran-2,3-xylylene in solution

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

Western Sydney University

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

18 Citations (Scopus)

Abstract

Benzofuran-2,3-xylylene 3b (2,3-dimethylene-2,3-dihydrobenzofuran) can be generated at -4-degrees-C in acetonitrile by treatment of 2-acetoxymethyl-3-triisopropylsilymethylbenzofuran (7b), available from 3-methylbenzofuran-2-carboxylic acid dianion (5) in two steps, with tetrabutylammonium fluoride. Trapping the xylylene 3b in situ using reactive Diels-Alder dienophiles gives high yields of the adducts 8 (2-substituted or 2,3-disubstituted 1,2,3,4-tetrahydrodibenzofurans).

Original language	English
Pages (from-to)	627-629
Number of pages	3
Journal	Synlett
Volume	1991
Issue number	9
DOIs	https://doi.org/10.1055/s-1991-20819
Publication status	Published - 1991

Keywords

alkaloids
photoelectron spectroscopy

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10.1055/s-1991-20819

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title = "A brief and mild method for the generation of Benzofuran-2,3-xylylene in solution",

abstract = "Benzofuran-2,3-xylylene 3b (2,3-dimethylene-2,3-dihydrobenzofuran) can be generated at -4-degrees-C in acetonitrile by treatment of 2-acetoxymethyl-3-triisopropylsilymethylbenzofuran (7b), available from 3-methylbenzofuran-2-carboxylic acid dianion (5) in two steps, with tetrabutylammonium fluoride. Trapping the xylylene 3b in situ using reactive Diels-Alder dienophiles gives high yields of the adducts 8 (2-substituted or 2,3-disubstituted 1,2,3,4-tetrahydrodibenzofurans).",

keywords = "alkaloids, photoelectron spectroscopy",

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

year = "1991",

doi = "10.1055/s-1991-20819",

language = "English",

volume = "1991",

pages = "627--629",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme",

number = "9",

}

TY - JOUR

T1 - A brief and mild method for the generation of Benzofuran-2,3-xylylene in solution

AU - Bedford, Simon B.

AU - Begley, Michael J.

AU - Cornwall, Philip

AU - Knight, David W.

PY - 1991

Y1 - 1991

N2 - Benzofuran-2,3-xylylene 3b (2,3-dimethylene-2,3-dihydrobenzofuran) can be generated at -4-degrees-C in acetonitrile by treatment of 2-acetoxymethyl-3-triisopropylsilymethylbenzofuran (7b), available from 3-methylbenzofuran-2-carboxylic acid dianion (5) in two steps, with tetrabutylammonium fluoride. Trapping the xylylene 3b in situ using reactive Diels-Alder dienophiles gives high yields of the adducts 8 (2-substituted or 2,3-disubstituted 1,2,3,4-tetrahydrodibenzofurans).

AB - Benzofuran-2,3-xylylene 3b (2,3-dimethylene-2,3-dihydrobenzofuran) can be generated at -4-degrees-C in acetonitrile by treatment of 2-acetoxymethyl-3-triisopropylsilymethylbenzofuran (7b), available from 3-methylbenzofuran-2-carboxylic acid dianion (5) in two steps, with tetrabutylammonium fluoride. Trapping the xylylene 3b in situ using reactive Diels-Alder dienophiles gives high yields of the adducts 8 (2-substituted or 2,3-disubstituted 1,2,3,4-tetrahydrodibenzofurans).

KW - alkaloids

KW - photoelectron spectroscopy

UR - http://handle.westernsydney.edu.au:8081/1959.7/uws:47289

U2 - 10.1055/s-1991-20819

DO - 10.1055/s-1991-20819

M3 - Article

SN - 0936-5214

VL - 1991

SP - 627

EP - 629

JO - Synlett

JF - Synlett

IS - 9

ER -

A brief and mild method for the generation of Benzofuran-2,3-xylylene in solution

Abstract

Keywords

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