The Reactions of Alkenes with Phenyl-<i>N</i>-triflylimino-λ<sup>3</sup>-iodane: Solvent and Oxidant Impact
2023
Mikhail Yu. Moskalik | Anton S. Ganin | Bagrat A. Shainyan
The reactions of alkenes with phenyl-<i>N</i>-triflylimino-λ<sup>3</sup>-iodane PhI=NTf (<b>1</b>) have been studied in different conditions. In methylene chloride, in the presence of <i>N</i>-halosuccinimides, the products of mono and bis-triflamidation were obtained. In MeCN, the product of bromotriflamidation (with NBS) with solvent interception or of bis-triflamidation (with NIS) is formed. The reaction with <i>trans</i>-stilbene in acetonitrile with NBS gave rise to cyclization to 2-methyl-4,5-diphenyl-1-triflyl-4,5-dihydro-1<i>H</i>-imidazole. In contrast, with NIS as an oxidant, both in CH<sub>2</sub>Cl<sub>2</sub> and MeCN, the major product was 2,3-diphenyl-1-triflylaziridine formed in good yield. With NBS, aziridine is also formed but as a minor product, the major one being a mixture of diastereomers of the product of bromotriflamidation. The reaction of compound <b>1</b> with vinylcyclohexane in methylene chloride affords the mixtures of regioisomers of the products of halotriflamidation, whereas in acetonitrile, the products of solvent interception and cyclization to the imidazoline are formed. A mechanism explaining the formation of all isolated products is proposed.
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