The Reaction of Hindered Phenols with Diazomethane

John S. Meek, Joanna S. Fowler, Pearle A. Monroe, Thomas J. Clark

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The reaction of 2,6-di-t-butyl-4-nitrophenol with diazomethane yields the nitronic ester exclusively, whereas 2,6-diisopropyl-4-nitrophenol reacts with diazomethane to give a mixture of the nitronic ester and the corresponding anisole. The reaction of 10-nitro-9-anthrone with diazomethane gives the monoxime of anthraquinone and formaldehyde. Silation of 2,6-di-t-butyl-4-nitrophenol with bis(trimethylsilyl)acetamide gives an unstable nitronic ester which rearranges to the trimethylsilyl ether.

Original languageEnglish
Pages (from-to)223-226
Number of pages4
JournalJournal of Organic Chemistry
Volume33
Issue number1
DOIs
StatePublished - 1 Jan 1968
Externally publishedYes

Fingerprint

Dive into the research topics of 'The Reaction of Hindered Phenols with Diazomethane'. Together they form a unique fingerprint.

Cite this