88374-07-6Relevant academic research and scientific papers
Efficient use of trimethylsulfonium methylsulfate as a reagent for the epoxidation of carbonyl-containing compounds
Forrester, Julie,Jones, Ray V. H.,Preston, Peter N.,Simpson, Elizabeth S. C.
, p. 3333 - 3335 (1999)
A process for the efficient conversion of trimethylsulfonium methylsulfate into dimethylsulfonium methanide, thence epoxides, has been devised. Thus dimethyl sulfate and dimethyl sulfide are caused to react in the presence of either a mineral acid or an o
Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate: implications for the synthesis of epoxides from aldehydes and ketones
Forrester, Julie,Jones, Ray V. H.,Preston, Peter N.,Simpson, Elizabeth S. C.
, p. 2289 - 2292 (2007/10/02)
The reaction between dimethyl sulfoxide (DMSO) and dimethyl sulfate has been monitored qualitatively by (1)H NMR spectroscopy.At reaction temperatures of 20, 50 and 90 deg C, the major product is methoxydimethylsulfonium methyl sulfate 5 whereas at 100 deg C the major product is trimethylsulfonium methyl sulfate 6 together with minor amounts of methoxydimethylsulfonium methyl sulfate; formaldehyde was qualitatively identified as a product by derivatization (2,4-dinitrophenylhydrazone).Treatment of the product ensuing from the latter reaction with potassium hydroxide, followed by addition of (separately) benzaldehyde and 1-(2,4-dichlorophenyl)pentane-1-one gave the expected epoxides 4a and 4b, respectively.
Simple, Inexpensive Synthesis of Oxiranes from Carbonyl Compounds. Generation of Sulfonium Ylides from the Ternary System Methanol-Sulfuric Acid-Dimethyl Sulfide
Forrester, Julie,Jones, Ray V. H,Preston, Peter N.,Simpson, Elisabeth S. C.
, p. 1937 - 1938 (2007/10/02)
Reaction conditions are described for the transformation of benzaldehyde and series of ketones into epoxides, in situ, in the ternary system: methanol-sulfuric acid-dimethyl sulfide.
