- THE ENE REACTION OF SINGLET OXYGEN: KINETIC AND PRODUCT EVIDENCE IN SUPPORT OF A PEREPOXIDE INTERMEDIATE
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The ene reaction of singlet oxygen (1O2) was examined using time-resolved techniques and by an intramolecular trapping reaction.The Eyring activation parameters reveal that the rate of the ene reaction of 1O2 with simple olefins is c
- Hurst, John R.,Wilson, Stephen L.,Schuster, Gary B.
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- Thermal Decomposition of Pentacarbonyl(1-acyloxyalkylidene)chromium(0) Complexes: Formation of Z-Enol Esters
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Pentacarbonyl(1-acyloxyalkylidene)chromium(0) complexes, formed in situ by reaction of the corresponding tetramethylammonium pentacarbonyl(1-oxoalkyl)chromate(1-) salts with carboxylic acid halides, affords enol esters in moderate to good yields. In all cases examined, the Z-enol ester was obtained as the major or exclusive isomer. Addition of 1 equiv of pyridine to the reaction mixture substantially improved the Z/E ratio and, in most cases, increased the chemical yield.
- S?derberg, Bj?rn C.,Liu, Jian,Ball, Thomas W.,Turbeville, Michael J.
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p. 5945 - 5952
(2007/10/03)
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- Allergenic α-Methylene-γ-butyrolactones. β-Hydroxy-α-methylene-γ-butyrolactones. 2. Syntheses from Ethyl 2-(Phenylthio)propionate and α-Acetoxy Aldehydes
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β-Hydroxy-and β-acetoxy-α-methylene-γ-butyrolactones were prepared from α-acetoxy aldehydes and ethyl 2-(phenylthio)propionate.Diastereomeric sulfides 8-11 were separated, oxidized, and thermally eliminated, leading to β-acetoxy-exo-methylene lactones 23-25 and to butenolides 26-28, depending on the configuration of the phenylsulfinyl group. β-Hydroxy lactones 19 were prepared by saponification of the β-acetoxy derivatives.
- Barbier, Pierre,Benezra, Claude
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p. 2705 - 2709
(2007/10/02)
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