1,3-methoxy rearrangement of masked o-benzoquinones: a novel synthesis of p-quinol ethers

Org Lett. 2007 Nov 8;9(23):4809-12. doi: 10.1021/ol702136r. Epub 2007 Oct 20.

Abstract

p-Quinol ethers are valuable synthons in synthetic organic chemistry. MOBs 1a-1i can be converted to p-quinol ethers 2a-2i in a highly efficient manner via 1,3-methoxy migration catalyzed by Lewis acids. The migration was found to be reversible and dependent on the electronic effect of substituent R3 of MOBs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry
  • Benzoquinones / chemistry*
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Hydroquinones / chemistry*
  • Methylation
  • Molecular Structure
  • Oxygen / chemistry*
  • Solvents

Substances

  • Acids
  • Benzoquinones
  • Ethers
  • Hydroquinones
  • Solvents
  • Oxygen