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Synthesis of 1,3‐Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
Author(s) -
Nagasawa Shota,
Sasano Yusuke,
Iwabuchi Yoshiharu
Publication year - 2016
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.201607752
Subject(s) - regioselectivity , chemistry , reactivity (psychology) , functional group , organic chemistry , polymer chemistry , medicinal chemistry , combinatorial chemistry , catalysis , polymer , medicine , alternative medicine , pathology
Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo‐ and regioselectivity. Herein, we report a convenient one‐pot process for this transformation that involves the unprecedented N‐preferential group transfer of N ‐oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.