Tetrahedron p. 1605 - 1610 (1989)
Update date:2022-08-25
Topics:
Moriarty, R. M.
Vaid, R. K.
Ravikumar, V. T.
Hopkins, T. E.
Farid, P.
Hypervalent iodine oxidation of various 5-substituted pyrazol-3(2H)-ones (1a-h) with iodobenzene diacetate or iodosobenzene in methanol results in fragmentative loss of molecular dinitrogen to yield methyl 2-alkynoates (2a-h).However, 5-methyl-4-substituted pyrazol-3(2H)-ones (3a-d) under similar conditions yield methyl 2,3-allenic esters (4a-d).Methyl 2,3-cycloalkadienoates (6a-e) are obtained by the oxidative cleavage of 4,5-polymethylene pyrazol-3(2H)-ones (5c-e) using iodobenzene diacetate or iodosobenzene in methanol. 5-Methyl-4,4-disubstituted pyrazol-3(2H)-ones (7a-b) were found not to undergo raction under similar conditions.The scope and mechanism of these reactions are discussed.
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