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Photooxygenation of Masked o‐ Benzoquinones: An Efficient Entry into Highly Functionalized Cyclopentenones from 2‐Methoxyphenols
Author(s) -
Kao TzuChiao,
Chuang Gary Jing,
Liao ChunChen
Publication year - 2008
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.200802130
Subject(s) - photooxygenation , singlet oxygen , cycloaddition , chemistry , singlet state , cyclopentenone , combinatorial chemistry , variety (cybernetics) , computer science , stereochemistry , oxygen , organic chemistry , catalysis , physics , artificial intelligence , nuclear physics , excited state
MOB tactics : A novel oxidation of masked o‐ benzoquinones (MOBs) 1 occurs by singlet‐oxygen‐triggered ring contraction to form cyclopentenone derivatives 2 and by [4+2] cycloaddition to give endoperoxides 3 . The competing pathways are directed by solvents and allow access to a variety of functionalized cyclopentenes.