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Updated: May 17, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Solvent-dependent photochemistry of 2,2,2-tribromoethyl-(2'-phenylacetate)
Derek M Denning1, Daniel E Falvey
1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
Abstract:
Photolysis (254 nm) of the title compound 1 produces a variety of stable products, which vary significantly with the nature of the solvent. Solvents that serve as efficient H atom donors (methanol, ethanol, isopropyl alcohol) favor products arising from a net reduction of one or more of the C-Br bonds. These include 2,2-dibromoethyl-(2'-phenylacetate) 2 and 2-bromoethyl-(2'-phenylacetate) 3. In the presence of nucleophiles, products such as 2-(2'-phenylacetoxy)acetic acid 5a and/or its ester derivatives are produced. Phenylacetic acid 6 is formed in some cases but under the conditions studied appears to be a minor product. The results are interpreted in terms of a general mechanism that features formation of an iso-tribromo intermediate 9 and/or a geminate radical-atom pair.
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