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Abstract
Oxidation of the chiral oxazoline 1 using 1.6 equivalents of MCPBA gives mainly the corresponding ring-opened nitroso compound 4 isolated as its dimer 5 together with an E/Z mixture of the isomeric oximes 2 and 3. Upon treatment of 1 with an excess of NO2 the product is the alkyl nitrate 23.
Highlights
Some time ago we described the oxidation of a range of chiral 2-thiazolines (4,5dihydrothiazoles) which was found to result in either S-oxidation to give thiazoline S,S-dioxides which were subject to subsequent hydrolytic ring-opening and disproportionation or else dehydrogenation to give thiazoles depending on the conditions used.[1]
2-oxazolines (4,5-dihydrooxazoles) are known to undergo oxidation to the corresponding oxaziridines with MCPBA and these may be isomerised to the corresponding oxazoline N-oxides on silica gel.[2]
The 4,4-dimethyloxazoline N-oxides formed in this way or by an alternative ring synthesis have been shown to be effective 1,3-dipoles.[3]
Summary
Some time ago we described the oxidation of a range of chiral 2-thiazolines (4,5dihydrothiazoles) which was found to result in either S-oxidation to give thiazoline S,S-dioxides which were subject to subsequent hydrolytic ring-opening and disproportionation or else dehydrogenation to give thiazoles depending on the conditions used.[1]. When a solution of the chiral oxazoline 1 in CH2Cl2 was treated with MCPBA (1.6 equiv.) at RT a deep blue-green colour developed which slowly faded.
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