Preparation and Rearrangement of Arylhydroxymethano[3]orthocyclo[5](1,8)naphthalenophanes

Autor:	Shin-ichiro Isobe, Tadashi Yonemitsu, Thies Thiemann, Shuntaro Mataka, Tsuyoshi Sawada, Kanji Kubo
Rok vydání:	2002
Předmět:	chemistry.chemical_compound Carbon atom chemistry Aryl Reagent Substituent Hydrobromic acid Nanotechnology General Chemistry Azulene Medicinal chemistry
Zdroj:	Bulletin of the Chemical Society of Japan. 75:773-779
ISSN:	1348-0634 0009-2673
Popis:	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.
Databáze:	OpenAIRE
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