Tandem Ring Expansion of Alkenyl Benzocyclobutenol Derivatives into Substituted Naphthols | Zendy

Hamura Toshiyuki | Zendy; Suzuki Takeaki | Zendy; Matsumoto Takashi | Zendy; Suzuki Keisuke | Zendy

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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 .

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