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

Fingerprint Dive into the research topics of 'Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate: Implications for the synthesis of epoxides from aldehydes and ketones'. Together they form a unique fingerprint.

  • Cite this