Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

J. R. Falck, D. K. Barma, Rachid Baati, Charles Mioskowski

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR < 4-MeOC6H4CH2OR < 3,4-(MEO)2C6H3CH2OR < 2,6-(MeO)2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Original languageEnglish (US)
Pages (from-to)1281-1283
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number7
DOIs
StatePublished - Apr 2 2001

Keywords

  • Chemoselectivity
  • Chromium
  • Cleavage reactions
  • Protecting groups
  • Reductions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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