Open AccessStrain-Promoted Oxidation of Methylenecyclopropane Derivatives using N-Hydroxyphthalimide and Molecular Oxygen in the Dark
Author(s) -
Thomas E. Anderson,
K. A. Woerpel
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02075
Subject(s) - chemistry , autoxidation , hydroxylamine , methylenecyclopropane , molecular oxygen , photochemistry , alkene , catalysis , oxygen , substrate (aquarium) , strain (injury) , organic chemistry , medicinal chemistry , medicine , oceanography , geology
The hydroperoxidation of alkylidenecyclopropanes and other strained alkenes using an N -hydroxylamine and molecular oxygen occurred in the absence of catalyst, initiator, or light. The oxidation reaction proceeds through a radical pathway that is initiated by autoxidation of the alkene substrate. The hydroperoxides were converted to their corresponding alcohols and ketones under mild conditions.