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Polar effects in free-radical reactions. Selectivity and reversibility in the homolytic benzylation of protonated heteroaromatic bases

✍ Scribed by Minisci, Francesco; Vismara, Elena; Morini, Giampiero; Fontana, Francesca; Levi, Silvio; Serravalle, Marco; Giordano, Claudio

Book ID: 120038576
Publisher: American Chemical Society
Year: 1986
Tongue: English
Weight: 514 KB
Volume: 51
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo00354a012

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## Abstract A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N‐oxyl radical (PINO) generated from __N__‐hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromat