The reaction of the CCl3O2˙ radical with indoles
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 555-562
- https://doi.org/10.1039/p29890000555
Abstract
In its reaction with indoles the CCl3O2˙ radical adds predominantly to the C(2)–C(3) double bond. Only a minor fraction accounts for one-electron oxidation. The 3-adduct undergoes rapid cleavage along the peroxidic bond while several rearrangement paths are indicated for the 2-adduct. In addition, the latter was found to break down into an indolyl radical cation in the presence of protons. The C(3) carbon adduct eventually reduces oxygen to O2 –˙. The major end products formed from indoles unsubstituted at the 3-position are indoxylic compounds while substantial amounts of open amides are found among the end products derived from 3-methylindoles.Keywords
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