O and S methylation of the ambident p-toluenesulfinate anion

John S. Meek, Joanna S. Fowler

Research output: Contribution to journalArticlepeer-review

97 Scopus citations

Abstract

The alkylation of the p-toluenesulfinate anion in methanol or dimethylformamide by methyl iodide, methyl sulfate, and methyl p-toluenesulfonate gives both methyl p-toluenesulfinate and methyl p-tolyl sulfone. Alkylation of the ambident anion with hard alkylating agents gives predominantly the ester, whereas a soft alkylating agent gives predominantly the sulfone.

Original languageEnglish
Pages (from-to)3422-3424
Number of pages3
JournalJournal of Organic Chemistry
Volume33
Issue number9
DOIs
StatePublished - 1 Aug 1968
Externally publishedYes

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