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The [2+2]‐Cycloaddition Reaction of Bisallenes: A Dramatic Substituent Effect
Author(s) -
Lu Ping,
Ma Shengming
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090271
Subject(s) - chemistry , substituent , cycloaddition , regioselectivity , allene , bicyclic molecule , toluene , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The bisallenes 1 possessing a phenylsulfonyl or n ‐butyl substituent at the internal position of allene moieties could be smoothly transformed to the bicyclo[5.2.0] or bicyclo[6.2.0] derivatives 2 in moderate to excellent yields with good regioselectivity upon refluxing in toluene. This [2+2]‐cycloaddition reaction shows an interesting substituent effect as unveiled by comparing with the results of unsubstituted substrates. However, further attention should be paid to the control of the regioselectivity of the [2+2]‐cycloaddition involving different CC bonds.