IMPROVED SYNTHESES OF 1H-BENZ[F]INDENE

1,3-Cyclopentadiene, excess sodium hydride, and alpha,alpha,alpha'-tribromo-o-xylene react to give 1H-benz[f]indene in a 25% yield. alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene, 2-cyclopenten-1-one, and excess sodium iodide react to from benz[f]indan-1-one. Lithium aluminum hydride r...

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Bibliographic Details
Published inSynlett no. 9; p. 642
Main Authors BECKER, CL, MCLAUGHLIN, ML
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTHRACENE
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Summary:1,3-Cyclopentadiene, excess sodium hydride, and alpha,alpha,alpha'-tribromo-o-xylene react to give 1H-benz[f]indene in a 25% yield. alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene, 2-cyclopenten-1-one, and excess sodium iodide react to from benz[f]indan-1-one. Lithium aluminum hydride reduction of benz[f]indan-1-one and dehydration of benz[f]indan-1-ol forms the title molecule in an overall yield of 40%.
ISSN:0936-5214
DOI:10.1055/s-1991-20824