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Photolysis of a Benzyne Precursor Studied by Time-Resolved FTIR Spectroscopy.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2016 Feb 05; Vol. 81 (3), pp. 1151-6. Date of Electronic Publication: 2016 Jan 22. - Publication Year :
- 2016
-
Abstract
- The 266 nm laser flash photolysis of phtaloyl peroxide (2) in liquid acetonitrile solution at room temperature has been investigated. Upon 266 nm laser irradiation, 2 is effectively photodecarboxylated leading to the formation of o-benzyne (1) and two equivalents of CO2, yet a small fraction of photolyzed 2 follows a different pathway leading to 6-oxocyclohexa-2,4-dienylideneketene (3) and one equivalent of CO2. Compound 3 is kinetically reactive and reacts in the microsecond time scale following a first-order kinetic law. The presence of 1 in the photolysis experiment is confirmed by trapping experiments with methyl 1-methylpyrrole-2-carboxylate (6). The Diels-Alder reaction between 1 and 6 occurs under the selected experimental conditions on a time scale shorter than 100 ms.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 81
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 26760219
- Full Text :
- https://doi.org/10.1021/acs.joc.5b02678