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Metal‐Free Epoxidation of Internal and Terminal Alkenes with tert‐Butyl Hydroperoxide/Isobutyraldehyde/Oxygen System
Author(s) -
Hong Mei,
Min Jie,
Wang Shifa
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800378
Subject(s) - isobutyraldehyde , chemistry , tert butyl hydroperoxide , reagent , selectivity , catalysis , oxygen , methacrolein , radical initiator , metal , photochemistry , organic chemistry , polymer , monomer , methacrylic acid , polymerization
The epoxidation of several alkenes was studied using oxygen as green oxidant, isobutyraldehyde (IBA) as co‐reagent and tert‐butyl hydroperoxide (TBHP) as radical initiator at mild conditions (60 o C, atmospheric pressure with an oxygen balloon). TBHP could accelerate the production of carbonyl radical and its peroxidation, without using a metal catalyst. The factors influencing the conversion of the substrates and selectivity of the epoxides have been well investigated. Under optimized reaction conditions, the epoxidation of linear terminal, cyclic and aromatic alkenes was evaluated. Most performed reactions were high selectivity for production of the corresponding epoxides.