A Direct Method for the Construction of Benzene Rings

Richard K. Hill, Robert M. Carlson

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Reaction of 1,4-diacetoxybutadiene with dienophiles at elevated temperatures yields, in many cases, aromatic products resulting from elimination of acetic acid from the first-formed Diels-Alder adducts. This reaction provides a direct synthesis of benzene rings, especially useful in the synthesis of unsymmetrical biphenyls. Dienophiles used successfully include quinones, β-nitrostyrenes, chalcones, and acetylenes. The reaction of acetylenic dienophiles with 1-acetoxybutadiene also affords aromatic products. The adduct of 1,4-diacetoxy-butadiene and benzonorbornadiene did not aromatize below temperatures of 450°, and then only with rearrangement, to yield dibenzocycloheptatriene.

Original languageEnglish (US)
Pages (from-to)2414-2417
Number of pages4
JournalJournal of Organic Chemistry
Volume30
Issue number7
DOIs
StatePublished - Jan 1 1965

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