Aldehydes and Ketones Epoxidation with Trimethylsulfonium Bromide in a Slightly Hydrated Solid-Liquid Medium

Abstract Trimethylsulfonium bromide used in low hydrated solid-liquid phase transfer conditions is a very efficient agent for aldehyde and ketone epoxidation.

[1]  R. Grée,et al.  Trimethylsulfonium Methylsulfate, A Simple and Efficient Epoxidizing Agent , 1985 .

[2]  A. Gaset,et al.  Synthesis of 2-Acylfurans in the Presence of Phosphonic Resins as Catalysts , 1983 .

[3]  M. Rosenberger,et al.  The Synthesis of β,γ‐ and α,β‐Unsaturated Aldehydes via Polyene Epoxides , 1980 .

[4]  D. Milstein,et al.  DIMERIZATION OF TERMINAL EPOXIDES BY HOMOGENEOUS TRANSITION METAL COMPLEXES. A NOVEL SYNTHESIS OF CARBOXYLIC ESTERS , 1978 .

[5]  A. Merz,et al.  Phase‐transfer‐catalyzed Production of Sulfur Ylides in an Aqueous System , 1973 .

[6]  Carl R. Johnson,et al.  CHEMISTRY OF SULFOXIDES AND RELATED COMPOUNDS PART 48, THE MECHANISM OF NUCLEOPHILIC ALKYLIDENE TRANSFER BY SULFONIUM AND OXOSULFONIUM YLIDES , 1973 .

[7]  Carl R. Johnson,et al.  Chemistry of sulfoxides and related compounds. XXXIV. Mechanism of sulfonium ylide reactions. Synthesis of cyclopropanes and oxiranes of high optical purity , 1971 .

[8]  M. Hatch.  Synthesis of oxiranes from aqueous solutions of simple alkyl, allyl, and benzylsulfonium salts , 1969 .

[9]  R. C. Corley,et al.  Steroids. LXXIX. Synthesis and reactions of oxiranes obtained from 3- and 17-keto steroids. , 1968, The Journal of organic chemistry.

[10]  R. G. Carlson,et al.  Stereochemistry of epoxidation of rigid methylenecyclohexane systems. Determination of stereochemistry of exocyclic epoxides in rigid cyclohexanes by nuclear magnetic resonance half band widths , 1967 .

[11]  E. Corey,et al.  Methylsulfinyl Carbanion (CH3-SO-CH2-). Formation and Applications to Organic Synthesis , 1965 .

[12]  V. Franzen,et al.  Umsetzung von Sulfonium-Yliden mit polaren Doppelbindungen† , 1963 .

[13]  A. Gaset,et al.  Biomass as a source of monomers: II — Synthesis of 2-furyloxirane , 1983 .

[14]  M. Julia,et al.  Alkylation des ions carboxylates par les sels de sulfonium: influence des sels de cuivre , 1983 .

[15]  A. Gaset,et al.  Epoxydation d'aldehydes et de cetones par un procede de transfert solide-liquide , 1982 .

[16]  S. Akaboshi,et al.  A CONVENIENT METHOD FOR A PREPARATION OF OXIRANES , 1977 .

[17]  W. Tagaki,et al.  Oxiran formation in the base-catalysed reaction of long-chain alkyldimethylsulphonium salts and carbonyl compounds in benzene–water , 1973 .

[18]  P. Sykes,et al.  Synthetic steroids. Part X. Preparation of (3S)- and (3R)-spiro-[5α-cholestane-3,2′-oxiran] and their corresponding 2α-methyl and 2,2-dimethyl analogues , 1970 .

[19]  R. C. Corley,et al.  Steroids LXXVI. Stereospecific formation of α- and β-epoxides in the reaction of dimethylsulfonium methylide and dimethylsulfoxonium methylide with dihydrotestosterone , 1965 .