Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 2
380
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Catalytic Oxidative Domino Degradation of Alkyl Phenols Towards 2- and 3-Substituted Muconolactones

, , , &
Pages 251-266 | Received 07 Jun 2008, Published online: 22 Dec 2008
 

Abstract

The catalytic oxidative domino degradation of phenols was investigated. Hydrogen peroxide (30% aq.) was used as an oxidant and 2,2′-dinitro-4,4′-ditrifluoromethyldiphenyl diselenide 4e as a catalyst. The products were muconic acid 5, and muconolactones muconolactones—5-carboxymethylfuran-2(5H)-ones 7 and 9. Phenols with alkyl groups at 2 or 4 positions of the benzene ring were converted regioselectively to corresponding muconolactones substituted at alkenylene ring carbon atoms. The reaction mechanism is proposed.

Notes

a Preparative yield.

b Unreacted substrate 1a was isolated almost quantitatively.

c 3,5-Di-tert-butyl-1,2-benzoquinone (3) was formed in up to 5.0% yield.

a Preparative yield. Data in parantheses were determined on 1H NMR analysis.

b Mixture of EZ and EE muconic acids were formed.

c 5a and 5b were determined on 1H NMR analysis in 1:3 ratio.

d 2-Methylmuconic acids 21a were determined on 1H NMR analysis in 1:1 ratio.

e EE-3-methylmuconic acid was formed.

f The reaction was prolonged to 72 h.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.