Reactions of anthracene hydride with styrene and stilbene oxide. Reduction in benzylic position via nucleophilic substitution

Helmut Stamm, Lin Pen-Yuan, Andreas Sommer, Anton Woderer

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6 Citations (Scopus)

Abstract

Nucleophilic ring opening of oxiranes 1 and 2 by the carbanion AH- ("anthracene hydride") proceeds rapidly giving rise to two isomeric products 3 and 5 from styrene oxide 1. In prolonged reactions, products with a 9-benzyl 9,10-dihydroanthracene structure (5, 6) are fragmented by an excess of carbanion to yield anthracene A and benzylic anions. The respective products 7 and 8 of reductive opening can be isolated in good yields with Na+ as gegen ion; however, they are transformed into styrenes with Li+. No fragmentation was observed in reactions of styrene oxide with xanthenyl anion Xan-.

Original languageEnglish
Pages (from-to)2571-2578
Number of pages8
JournalTetrahedron
Volume45
Issue number9
DOIs
Publication statusPublished - 1989
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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