Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate

Implications for the synthesis of epoxides from aldehydes and ketones

Julie Forrester, R. V H Jones, Peter N. Preston, E. S C Simpson

Research output: Contribution to journalArticle

Abstract

The reaction between dimethyl sulfoxide (DMSO) and dimethyl sulfate has been monitored qualitatively by 1H NMR spectroscopy. At reaction temperatures of 20, 50 and 90°C, the major product is methoxydimethylsulfonium methyl sulfate 5 whereas at 100°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 derivatisation (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)pentan-1-one gave the expected epoxides 4a and 4b, respectively.

Original languageEnglish
Pages (from-to)2289-2291
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number18
Publication statusPublished - 1995

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Epoxy Compounds
Dimethyl Sulfoxide
Ketones
Aldehydes
Cations
Formaldehyde
Nuclear magnetic resonance spectroscopy
trimethylsulfonium
methyl sulfate
dimethyl sulfate
Temperature

Cite this

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abstract = "The reaction between dimethyl sulfoxide (DMSO) and dimethyl sulfate has been monitored qualitatively by 1H NMR spectroscopy. At reaction temperatures of 20, 50 and 90°C, the major product is methoxydimethylsulfonium methyl sulfate 5 whereas at 100°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 derivatisation (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)pentan-1-one gave the expected epoxides 4a and 4b, respectively.",
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Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate : Implications for the synthesis of epoxides from aldehydes and ketones. / Forrester, Julie; Jones, R. V H; Preston, Peter N.; Simpson, E. S C.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 18, 1995, p. 2289-2291.

Research output: Contribution to journalArticle

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T1 - Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate

T2 - Implications for the synthesis of epoxides from aldehydes and ketones

AU - Forrester, Julie

AU - Jones, R. V H

AU - Preston, Peter N.

AU - Simpson, E. S C

PY - 1995

Y1 - 1995

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