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Mechanism and Scope of the Mn III ‐Initiated Oxidation of β‐Ketocarbonyl Compounds: Furan Synthesis
Author(s) -
Wang Chao,
Li Zhilong,
Ju Yeming,
Koo Sangho
Publication year - 2012
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.201201194
Subject(s) - chemistry , furan , dioxetane , allylic rearrangement , intramolecular force , thermal decomposition , photochemistry , catalysis , radical , medicinal chemistry , decomposition , organic chemistry , chemiluminescence
Unless the Mn III ‐produced carbon‐radical from β‐ketocarbonyl compounds undergoes smooth intramolecular addition to alkenes, it traps molecular oxygen in the reaction medium to produce a peroxy radical, which reacts with the neighbouring carbonyl group to form 1,2‐dioxetane. Thermal decomposition of 1,2‐dioxetane completes the oxidation to produce α‐oxo ester. This oxidation seems to be general at 50 °C under aerobic conditions, and can be catalytic for Mn III in AcOH with ultrasonic irradiation. Thus, the development of a new synthetic method for diversely substituted furans has been accomplished based on a couple of the Mn III ‐initiated domino oxidation of β‐ketocarbonyl compounds with a suitable α‐allylic substitution.