Photolabile protection of alcohols, phenols, and carboxylic acids with 3-hydroxy-2-naphthalenemethanol

J Org Chem. 2008 Oct 3;73(19):7611-5. doi: 10.1021/jo801302m. Epub 2008 Sep 10.

Abstract

Irradiation of alcohols, phenols, and carboxylic acids "caged" with the (3-hydroxy-2-naphthalenyl)methyl group results in fast (k(release) approximately = 10(5) s(-1)) release of the substrates with good quantum (Phi = 0.17-0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (k(H2O) = 144 +/- 11 s(-1)) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide intermediate can be also trapped by other nucleophiles or converted into a photostable Diels-Alder adduct with ethyl vinyl ether.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemistry*
  • Carboxylic Acids / chemistry*
  • Indolequinones
  • Naphthalenes / chemistry*
  • Phenols / chemistry*
  • Photochemistry / methods*
  • Water / chemistry

Substances

  • Alcohols
  • Carboxylic Acids
  • Indolequinones
  • Naphthalenes
  • Phenols
  • Water
  • quinone methide
  • 2-naphthalenemethanol