Preparation and rearrangement of arylhydroxymethano[3]orthocyclo[5](1,8)naphthalenophanes

Shin Ichiro Isobe, Kanji Kubo, Thies Thiemann, Tsuyoshi Sawada, Tadashi Yonemitsu, Shuntaro Mataka

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Arylhydroxymethano[3]orthocyclo[5](1,8)naphthalenophanes 11, which possess a rigid boat-chair conformation, were prepared by the reaction of 9,10-benzo-3,4,5-[1,8]naphthobicyclo[5.4.1]dodecan-3,9-dien-12-one 8c with aryllithium reagents and treated with hydrobromic acid in dioxane. The intermediary cation generated from 11 rearranged either to a benzo[cd]azulene system of type 12 or to a tricyclic system containing a cyclopropane-unit of type 13, depending on the nature of the aryl substituent on the bridging carbon atom.

Original languageEnglish
Pages (from-to)773-779
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume75
Issue number4
DOIs
Publication statusPublished - 2002
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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