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Cationic Carbenoid Rearrangement of 2‐Phenyl Substituted gem ‐Dihalogenospiropentanes
Author(s) -
Sedenkova Kseniya N.,
Averina Elena B.,
Grishin Yuri K.,
Rybakov Victor B.,
Kuznetzova Tamara S.,
Zefirov Nikolay S.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000427
Subject(s) - carbenoid , chemistry , methyllithium , cationic polymerization , scope (computer science) , cope rearrangement , stereochemistry , medicinal chemistry , organic chemistry , catalysis , rhodium , computer science , programming language
Abstract The series of 2‐phenyl‐ and 2,2‐diphenyl gem ‐dihalogenospiropentanes were employed as model compounds to study the carbenoid rearrangement with the use of methyllithium. The scope and limitations of this skeletal rearrangement are outlined and its mechanism is discussed.