1976
DOI: 10.1021/jo00886a005
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Reduction of 1,3-diphenyl-2,2-dihaloaziridines with tri-n-butyltin hydride

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1977
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Cited by 30 publications
(12 citation statements)
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“…16 Yamanaka has also demonstrated the formation of halogenated aziridines via aziridinyl radical intermediates. 17 Selective reduction of 2,2-dihalogenated aziridines with H-SnBu 3 through a radical chain reaction affords the dehalogenated aziridine via a carbon-centered radical species.…”
Section: Introductionmentioning
confidence: 99%
“…16 Yamanaka has also demonstrated the formation of halogenated aziridines via aziridinyl radical intermediates. 17 Selective reduction of 2,2-dihalogenated aziridines with H-SnBu 3 through a radical chain reaction affords the dehalogenated aziridine via a carbon-centered radical species.…”
Section: Introductionmentioning
confidence: 99%
“…6 Pioneering work in the formation of monochloroaziridines was reported by Deyrup and co-workers; a monochloroaziridine was generated by the reaction of dichloromethyllithium with N -benzylideneaniline at low temperatures, affording the cis -chloroaziridine (Figure 1A). 9a Since this seminal investigation, α-chloroaziridines have been accessed via reductive halogenation from gem -dihalogented aziridines, 10 addition of acid chlorides across 2 H -azirines, 11 nitrene addition to chloroalkenes, 12 and trapping of metalated aziridines with an electrophilic source of chlorine (Figure 1B). 13 Chlorinated aziridines have been shown to undergo nucleophilic displacement of chloride with a variety of nucleophiles including NaOMe, NaCN and LiAlH 4 , leaving the aziridine intact.…”
Section: Introductionmentioning
confidence: 99%
“…The present article reports on our first results of asymmetric synthesis of fluorinated DOI: 10.1134 prop-2-yn-1-amines from enantiomerically pure imines through chiral fluoroaziridines. Monofluoroaziridines can be obtained in different ways: by reaction of fluorocarbene with imines [33,34], by reduction of halofluoroaziridines with Bu 3 SnH [35,36], and by cyclization of β-fluoro-β-bromo(chloro) amines in the presence of bases [37,38]. The two latter procedures imply basic conditions, so that they are unsuitable for the synthesis of nonracemic compounds derived from amino acids.…”
mentioning
confidence: 99%