4.2 Article

Effect of aromaticity on the rate of azaquinone methide-mediated release of benzylic phenols

Journal

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 26, Issue 7, Pages 608-610

Publisher

WILEY-BLACKWELL
DOI: 10.1002/poc.3129

Keywords

aromaticity; azaquinone methide; controlled release; solvent effects

Funding

  1. American Chemical Society [51618-DNI7]
  2. Arnold and Mabel Beckman Foundation
  3. Camille and Henry Dreyfus Foundation
  4. Alfred P. Sloan Research Fellows Program

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Herein we use small molecule models of stimuli-induced degradable/depolymerizable polymers to demonstrate that less aromatic releasing units provide faster rates of azaquinone methide-mediated release of benzylic phenols (a surrogate for a group released in a polymer) than highly aromatic releasing units. Copyright (c) 2013 John Wiley & Sons, Ltd.

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