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Green Chem., 2004, 6, 142 - 146, DOI: 10.1039/b312849k
A practical improvement of odorless Corey–Kim and Swern oxidations
Kiyoharu Nishide, Pranab K. Patra, Manabu Matoba, Kandasamy Shanmugasundaram and Manabu Node
Methyl 6-morpholinohexyl sulfide ( 3a, MMS) and methyl 6-morpholinohexyl sulfoxide ( 7, MMSO) have been employed as efficient odorless substitutes for dimethyl sulfide (DMS) and dimethyl sulfoxide (DMSO) in Corey–Kim and Swern oxidations, respectively. The oxidation products and the byproduct 3a are easily separable by simple aqueous extraction. The Corey–Kim oxidation was studied in various solvents. The utility of the odorless 6-morpholinohexan-1-thiol ( 2a) in the dealkylation of phenyl ethers and methyl esters is also presented.
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