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The Synthesis and Chemistry of 8‐Substituted Bicyclo[5.1.0]oct‐1(8)‐ene
Author(s) -
Lee GonAnn,
Chen Calvin PingKuang,
Chen MeiYun
Publication year - 1998
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199800060
Subject(s) - chemistry , bicyclic molecule , ene reaction , cyclopropene , cyclopentadiene , adduct , octane , bridged compounds , medicinal chemistry , nucleophile , cyclooctene , nucleophilic substitution , organic chemistry , catalysis
8‐Bromobicyclo[5.1.0]oct‐1(8)‐cne (7), an intermediate for the preparation of 8‐substituted bicyclo[5.1.0]oct‐1(8)‐enes, was synthesized by denomination of 1,8,8‐tribromobicyclo[5.1.0]octane (6). Compound 7 underwent bromo‐lithium exchange followed by nucleophilic substitution reactions to generate bicyclo[5.1.0]oct‐1(8)‐ene (5), 8‐methylbicyclo[5.1.0]oct‐1(8)‐ene (10), and 8‐trimethylsilylbicyclo[5.1.0]oct‐1(8)‐ene (11). The bicyclic cyclopropenes 7, 5, 10, and 11 reacted with cyclopentadiene to form adducts 12, 13, 14, and 15, respectively. All of these Diels‐Alder adducts are endo‐exo isomers (endo‐addition from the view of the cyclopropene and exo‐addition from the view of the cyclooctene).