- Oxidation of Vicinal Diols to α-Dicarbonyl Compounds by Trifluoroacetic Anhydride "Activated" Dimethyl Sulfoxide
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Trifluoroacetic anhydride "activated" dimethyl sulfoxide is an effective oxidant for the conversion of vicinal diols into the corresponding α-dicarbonyl compounds or products derived therefrom.Unlike the Swern oxidant, the title reagent system gives good yields of products derived from halogenated substrates.The method has permitted syntheses of previously inaccessible compounds including tropolones, a ?-homo-o-benzoquinone, and a "hyperreactive" α-keto aldehyde.
- Amon, Catherine M.,Banwell, Martin G.,Gravatt, G.Lance
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- CONVENIENT PREPARATION OF 1,2-CYCLOHEXANEDIONES
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1,2-Cyclohexanedione and 3-alkyl-1,2-cyclohexanediones were prepared in good to excellent yields from the corresponding 2,6-dibromocyclohexanones by treatment with aqueous NaOH.
- Utaka, Masanori,Matsushita, Seishiro,Takeda, Akira
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- VOLATILE CONSTITUENTS OF BALSAM POPLAR: THE PHENOL GLYCOSIDE CONNECTION
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Key Word Index - Populus balsamifera; Salicaceae; balsam poplar; phenol glycosides; 6-hydroxycyclohex-2-enone; cyclohexan-1,2-dione; salicortin; trichocarpin; trichocarpigenin.The volatile metabolites of balsam poplar winter-domant buds are a complex array of mono- and sesquiterpenoids with 1,8-cineol, trans-nerolidol and (+)-(1R,1'R)-α-bisabolol being the major components.On the other hand the volatiles of internodes (stems between buds) consist mainly of salicaldehyde and (+)-6-hydroxycyclohexanone with minor amounts of cyclohexan-1,2-dione and an unidentified compound.This is the first report of these cyclohexanones as natural products; salicortin, a phenol glycoside, appears to be their biosynthetic precursor.A second phenol glycoside, trichocarpin, is present in poplar internodes; and it is the progenitor of trichocarpigenin (benzyl gentisate), an easily formed artifact.
- Mattes, Benjamin R.,Clausen, Thomas P.,Reichardt, Paul B.
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- Microwave-assisted synthesis of α-hydroxy ketone and α-diketone and pyrazine derivatives from α-halo and α,α′-dibromo ketone
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A novel reaction of α-halo ketone (α-bromo and α-chloro ketone) with irradiation under microwave gave the corresponding α-hydroxyketone and pyrazine derivative in good yields. In the case of α,α′-dibromo ketone, α-diketone was obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxyketone, α-diketone, α-chloro ketone and pyrazine derivative.
- Utsukihara, Takamitsu,Nakamura, Hiroaki,Watanabe, Masashige,Akira Horiuchi
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- Acid Catalyzed Alcoholysis of an Epoxide and Reactions of Products on Contact with Silica Gel
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The alcoholysis of epoxide 1 in acidic methanol leads to various products; one of these - hydroxymethoxyketone 7 - rearranges to the isomeric ketone 14 on contact with silica gel. Keywords: Cleavage of Epoxide, Rearrangement
- Habermehl, Gerhard G.,Wippermann, Irene
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p. 1421 - 1424
(2007/10/02)
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- PHOTOOXYGENATION OF 1,2-BIS(SILYLOXY)CYCLOALKENES
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The reaction of singlet oxygen with O-silylated cyclic enediols 1a, b afforded as ene products the hydroperoxy silyl enol ethers 3a,b and as cleavage products the silyl esters 4a,b; the latter presumably derived from rearrangement of the intermediary sily
- Adam, Waldemar,Wang, Xiaoheng
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p. 1245 - 1248
(2007/10/02)
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- A New Synthesis of 3-Alkyl-1,2-cyclohexanediones from 2-Alkylcyclohexanones Using Iodine/Copper(II) Acetate
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The reactions of 2-alkyl-, 2,5-dimethyl-, and 3,3,5-trimethylcyclohexanone with iodine/copper(II) acetate in boiling aqueous acetic acid gave the respective 3-alkyl-, 3,6-dimethyl-, and 3,5,5-trimethyl-1,2-cyclohexanediones in 40-70percent yields.This new
- Horiuchi, C. Akira,Kiyomiya, Hiroshi,Takahashi, Masaaki,Suzuki, Yasuto
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p. 785 - 786
(2007/10/02)
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- OXIDATION OF THE α-KETOL AND ENONE DERIVATIVES OF CYCLOHEXANONE BY TETRAZOLIUM SALTS
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A new red-ox reaction, leading to the respective keto derivatives from α-ketol and enone derivatives of cyclohexanone, is reported.
- Jasiczak, Jan
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p. 4323 - 4326
(2007/10/02)
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