α-及びβ-ピロネンの水和及び酸化生成物について

概要

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The hydration and oxidation of α- and β-pyronenes (1), (2) with chlorinated acetic acids (mono-, di- or trichloroacetic acid), in polar aprotic solvents [dimethyl sulfoxide (DMSO), N, N-dimethyl formamide (DMF), sulfolane (SF), and ethylene carbonate (EC)] or lead tetraacetate were investigated. The results obtained are as follows : Hydration of (1) gave 1, 2, 6, 6-tetramethyl-2-cyclohexen-1 β-ol (10) with good selectivity. In EC, the oxidation of (1) gave 2, 3, 4, 4-tetramethyl-2, 5-cyclohexadien-1-on (9) as the main product (maximum in a 91% conversion). 1, 2, 3, 4-Tetramethyl-benzene (5) and cis-2-hydroxy-5, 5, 6-trimethyl-3, 6-cyclohexadienemethanol (23) were obtained as two main products by the oxidation of (1) with lead tetraacetate. In DMSO, the oxidation of (2) gave 1, 2, 6, 6-tetramethyl-1, 3-cyclohexadien-5-on (8) as the major product. The oxidation of (2) with lead tetraacetate gave cis-1, 2, 6, 6-tetramethyl-3-cyclohexene-1, 2-diol (22) in high conversion (71% at optimum). The reaction products were identified by comparing their of IR, NMR and GC-MS spectra with those of the authentic samples.
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