A BRIEF AND MILD METHOD FOR THE GENERATION OF BENZOFURAN-2,3-XYLYLENE IN SOLUTION

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....

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Bibliographic Details
Published inSynlett no. 9; pp. 627 - 629
Main Authors BEDFORD, SB, BEGLEY, MJ, CORNWALL, P, KNIGHT, DW
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORTHO-XYLYLENE
CYCLOADDITION REACTIONS
FLASH VACUUM PYROLYSIS
STRATEGY
ORTHO-QUINODIMETHANES
2,3-DIHYDRO-2,3-BIS-(METHYLENE)THIOPHENES
2,3-DIMETHYLENE-2,3-DIHYDROTHIOPHENE
CHEMISTRY
PHOTOELECTRON-SPECTROSCOPY
ALKALOIDS
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Summary: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).
ISSN:0936-5214
DOI:10.1055/s-1991-20819