39038-72-7Relevant academic research and scientific papers
2H-AZIRINES EN MILIEU ACIDE. FORMATION ET REACTIVITE D'α-IMINOCARBENIUMS
Flamming, R.,Lacombe, S.,Laurent, A.,Maquestiau, A.,Marquet, B.,Novkova, S.
, p. 315 - 328 (2007/10/02)
Reactivity of protonated azirines is studied in solution and by chemical ionization in the gazeous phase.Azirinium ion produces an α-iminocarbenium ; its reactivity is studied.Mass spectrometry (CID- MIKE technic) proves the rearrangement of the α-iminocarbenium in a nitrilium ion.This nitrilium can also be obtained in solution.
ACTION DE L'ACIDE FLUORHYDRIQUE SUR LES AZIRINES: SYNTHESE D'α-FLUOROCETONES ET DE DIFLUOROAMINES - ETUDE DE L'ORIENTATION DE LA REACTION
Alvernhe, Gerard,Lacombe, Sylvie,Laurent, Andre
, p. 1437 - 1440 (2007/10/02)
Addition of Olah's reagent in benzene or methylene chloride to azirines leads to the formation of difluoroamines or α-fluoroketones.This reaction has been applied to the synthesis of 17 α-fluoropregnolone.The formation of fluoroketone proceeds via a cationic intermediate.Yield is improved when using a more nucleophilic fluorinating reagent obtained by addition of triethylamine to Olah's reagent.
New Convenient Synthesis of β,β-Difluoro Amines and β,β-Difluoro-α-amino Acid Alkyl Esters by the Addition of Hydrogen Fluoride to 1-Azirines
Wade, Tamsir N.,Kheribet, Rabia
, p. 5333 - 5335 (2007/10/02)
The reaction of hydrogen fluoride in pyridine solution with a series of substituted 1-azirines (1) was investigated. β,β-Difluoro amines (4) were obtained in good yields.The exceptions are the cases of 2-phenyl-3-methyl-1-azirine (1b) and 2,3-diphenyl-1-azirine (1c) for which the direct formation of a stabilized carbocation (6) from the azirinium ion 2 is probable.The former gave 54 percent of a pyrazine (11b) and 5 percent of α-fluoropropiophenone (9b) along with 20 percent of difluoro amine 4b, while the latter afforded only the corresponding α-fluoro ketone (9c).A mechanism is suggested.
