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

Research output: Contribution to journalArticle

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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styrene oxide
Hydrides
Anions
Styrenes
Substitution reactions
Epoxy Compounds
Reaction products
Ions
stilbene oxide
anthracene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Reactions of anthracene hydride with styrene and stilbene oxide. Reduction in benzylic position via nucleophilic substitution. / Stamm, Helmut; Pen-Yuan, Lin; Sommer, Andreas; Woderer, Anton.

In: Tetrahedron, Vol. 45, No. 9, 1989, p. 2571-2578.

Research output: Contribution to journalArticle

Stamm, Helmut ; Pen-Yuan, Lin ; Sommer, Andreas ; Woderer, Anton. / Reactions of anthracene hydride with styrene and stilbene oxide. Reduction in benzylic position via nucleophilic substitution. In: Tetrahedron. 1989 ; Vol. 45, No. 9. pp. 2571-2578.
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