Journal of the Chemical Society. Perkin transactions I p. 2059 - 2064 (1992)
Update date:2022-08-11
Topics:
Brehm, Lotte
Johansen, Joergen S.
Krogsgaard-Larsen, Povl
Treatment of ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate 4 with hydroxylamine under basic conditions gave 5-tert-butyl-4-methylisoxazol-3-ol 5 and a tautomeric mixture of 3-tert-butyl-4-methylisoxazol-5(2H)-one 6 and (RS)-3-tert-butyl-4-methylisoxazol-5(4H)-one 7.During the attempts to crystallize the inseparable mixture of tautomers 6 and 7 two other compounds, (RS)-3-tert-butyl-4-hydroxy-4-methylisoxazol-5(4H)-one 8 and (RS,RS)-3,3'-di-tert-butyl-4,4'-dimethyl-<4,4'-biisoxazole>-5(4H),5'(4'H)-dione 9, were progressively formed.The structure of compounds 8 and 9 were established by X-ray analyses.Compounds 8 and 9 are proposed to be formed by oxidation of compound 7 with oxygen, but the mechanisms underlying these two oxidative processes are unknown.
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