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Tandem Ring Expansion of Alkenyl Benzocyclobutenol Derivatives into Substituted Naphthols
Author(s) -
Hamura Toshiyuki,
Suzuki Takeaki,
Matsumoto Takashi,
Suzuki Keisuke
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602428
Subject(s) - ring (chemistry) , tandem , chemistry , stereochemistry , medicinal chemistry , organic chemistry , materials science , composite material
Twice expanded : Substituted naphthols were prepared in a novel synthetic route starting from alkenyl benzocyclobutenol derivatives. The conversion includes two successive ring‐enlargement processes ( A → B → C ; see scheme). The halonium ion (X + ) induces expansion of the four‐membered ring to a five‐membered ring, and SmI 2 promotes the expansion of the five‐membered ring to the six‐membered ring with concomitant elimination of ROSmI 2 .