Synthesis of Selenoaziridines: A Study on Stereochemical Outcomes of the Reaction of Aziridine Radicals and Anions Generated from Iodoaziridines | Zendy

Tom Boultwood | Zendy; James A. Bull | Zendy

Open Access

Synthesis of Selenoaziridines: A Study on Stereochemical Outcomes of the Reaction of Aziridine Radicals and Anions Generated from Iodoaziridines

Author(s) -

Tom Boultwood,

James A. Bull

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b03019

Subject(s) - aziridine , radical , chemistry , diselenide , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , ring (chemistry) , selenium

The synthesis of a new functional group in the form of selenyl-substituted aziridines is described. Selenoaziridines are stereoselectively prepared by functionalization of intact aziridine precursors involving radical and anionic intermediates. Radicals are generated from cis - N -Ts iodoaziridines by activation of the C-I bond using alkoxides as a source of single electrons. These form predominantly trans -substituted selenoaziridines dependent on the size of the diselenide. cis -Aziridinyllithiums generated by Li-I exchange also react with diselenides stereospecifically to form a range of cis -selenoaziridines. Proposals for the stereochemical outcome are presented.

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