1-[3-(Diethylamino)phenyl]ethyl (DEAPE): A Photolabile Protecting Group for Hydroxyl and Carboxyl Groups

Academic Article

Abstract

  • Copyright © 2018 American Chemical Society. Herein we demonstrate that the photolabile protecting group (PPG), the 1-[3-(diethylamino)-phenyl]ethyl (DEAPE) group, has dramatically different photochemical properties from the parent 3-(diethylamino)benzyl (DEABn) PPG. The new PPG, derived from DEABn by adding a methyl group to the benzylic carbon, has similar reactivity as DEABn in releasing alcohol in MeCN/water; however, it is more efficient than DEABn in releasing carboxylic acid. In particular, it can release carboxylic acid efficiently in aprotic solvents and the PPG itself converts to 3-diethylaminostyrene. Photochemical removal of DEAPE can also be conveniently carried out with sunlight. The results in this work suggest that there probably exist multiple reaction pathways in cleaving the benzylic C-O bond and they can be affected by the benzylic substitution and the reaction conditions.
  • Published In

    Digital Object Identifier (doi)

    Author List

  • Ding X; Wang P
  • Start Page

  • 10736
  • End Page

  • 10742
  • Volume

  • 83
  • Issue

  • 18