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The Synthesis and Trapping of 1‐Naphthylcyclopropenes
Author(s) -
Lee GonAnn,
Tsai RuTing,
Wang WenChieh,
Liu YuTing
Publication year - 2010
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.201000111
Subject(s) - chemistry , cyclopentadiene , adduct , trimethylsilyl , lithium (medication) , medicinal chemistry , trapping , organic chemistry , catalysis , medicine , ecology , biology , endocrinology
Abstract 1‐Bromo‐2‐naphthylcyclopropene ( 8 ), an intermediate for the preparation of 1‐substituted 2‐naphth‐ylcyclopropenes, was synthesized by debromination of 1,1,2‐tribromo‐2‐naphthylcyclopropane ( 7 ). Compound 8 underwent bromo‐lithium exchange followed by nuclephilic substitution reactions to generate 1‐trimethylsilyl‐2‐naphthylcyclopropene ( 11 ) and 1‐naphthylcyclopropene ( 12 ). The cyclopropenes 8 , 11 , and 12 reacted with cyclopentadiene to form adducts 9 , 13 , and 14 , respectively. All of these Diels‐Alder adducts are endo isomers.