Substituent effect on the selectivity of [3.3]Orthoanthracenophanes in the Diels-Alder reaction with N-(p-substituted phenyl)maleimides

Shuntaro Mataka, Ma Jiang, Thies Thiemann, Takao Mimura, Tsuyoshi Sawada, Masashi Tashiro

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Diels-Alder reactions of benzo- and naphtho-[3.3]orthoanthracenophanes 1a-b with N-(p-nitro, chloro or methoxy-substituted phenyl) maleimides 2a-c were investigated. In most cases, approximately equal amounts of inside-adduct 3 and outside-adducts (4 + 5) were obtained except for the outside-selective addition reaction of naphthophane 1b with p-nitro derivative 2a. Of the outside- the endo-adduct 4 was formed predominantly in all cases. Especially, the reaction of 1b afforded endo-adducts 4ba-bc almost exclusively. These facts suggest that the interaction between the phenyl group of 2 and the part of the anthraceno-unit closest to the underlying naphtho/benzo-moiety of 1 leads to a greater tendency toward endo-orientation.

Original languageEnglish
Pages (from-to)6817-6824
Number of pages8
JournalTetrahedron
Volume53
Issue number20
DOIs
Publication statusPublished - May 19 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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