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• W1533307517 abstract "Abstract 2,2,2-Trimethoxy-4,5-dimethyl-2,2-dihydro-1,3,2-dioxaphospholene, made from trimethyl phosphite and biacetyl, reacted with crotonaldehyde and gave 2,2,2-trimethoxy-4β-methyl-4α-acetyl-5α-( trans -1-propenyl) 2,2-dihydro-1,3,2-dioxaphospholane. The hydrolyses of the phospholane by one mole equivalent of water in aprotic solvents and by an excess of water were studied. Two hydrolytic pathways were observed at 20°. (1) A substitution of the OMe groups on phosphorus by OH groups. This led to 5-methyl-2-heptene-4,5-diol-6-one-(5-dihydrogen phosphate), which underwent a relatively slow isomerization to the corresponding 4-dihydrogen phosphate. (2) An attack by water on the allylic carbon, with CO bond fission. This led to the formation of trimethyl phosphate and 5-methyl-2-heptene-4,5-diol-6-one. At 100°, the dihydrogen phosphate ester lost phosphoric acid and gave an unsaturated dihydroxy-ketone. Methanolysis of the phospholane produced trimethyl phosphate and 4-methoxy-5-methyl-2-heptene-5-ol-6-one byCO bond fission." @default.
• W1533307517 created "2016-06-24" @default.
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• W1533307517 date "1968-01-01" @default.
• W1533307517 modified "2023-10-12" @default.
• W1533307517 title "Trialkyl phosphites as reagents in the carbon-carbon condensations of α-diketones with α,β-unsaturated aldehydes" @default.
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• W1533307517 doi "https://doi.org/10.1016/s0040-4020(01)98722-8" @default.
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