Aromatic ring-system controls π-facial selectivity in Diels-Alder reactions of [3.3]orthoanthracenophanes

Shuntaro Mataka, Jiang Ma, Thies Thiemann, Jerzy M. Rudziñski, Tsuyoshi Sawada, Masashi Tashiro

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The Diels-Alder reaction of layered [3.3]orthoanthracenophanes with electrondashpoor dienophiles is studied. Of special interest is the anthracenonaphthophane, which was found to add naphthoquinone, maleic anhydride and maleimide favorably from the inside face and N-phenyltriazolindione and dimethyl azodicarboxylate to the outside.

Original languageEnglish
Pages (from-to)6105-6108
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number34
DOIs
Publication statusPublished - Aug 21 1995
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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