TY - JOUR
T1 - Preparation and rearrangement of arylhydroxymethano[3]orthocyclo[5](1,8)naphthalenophanes
AU - Isobe, Shin Ichiro
AU - Kubo, Kanji
AU - Thiemann, Thies
AU - Sawada, Tsuyoshi
AU - Yonemitsu, Tadashi
AU - Mataka, Shuntaro
PY - 2002
Y1 - 2002
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.75.773
DO - 10.1246/bcsj.75.773
M3 - Article
AN - SCOPUS:0036090292
SN - 0009-2673
VL - 75
SP - 773
EP - 779
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 4
ER -