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- aggregation classification "A1".
- aggregation creator B173915.
- aggregation creator B173916.
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- aggregation date "2010".
- aggregation format "application/pdf".
- aggregation hasFormat 1028905.bibtex.
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- aggregation isPartOf urn:issn:1434-193X.
- aggregation language "eng".
- aggregation rights "I have transferred the copyright for this publication to the publisher".
- aggregation subject "Physics and Astronomy".
- aggregation title "Systematic study of halide-induced ring opening of 2-substituted aziridinium salts and theoretical rationalization of the reaction pathways".
- aggregation abstract "The ring-opening reactions of 2-alkyl-substituted 1,1-bis(arylmethyl)- and 1-methyl-1-(1-phenylethyl)aziridinium salts with fluoride, chloride, bromide and iodide in acetonitrile have been evaluated for the first time in a systematic way. The reactions with fluoride afforded regioisomeric mixtures of primary and secondary fluorides, whereas secondary β-chloro, β-bromo and β-iodo amines were obtained as the sole reaction products from the corresponding halides by regiospecific ring opening at the substituted position. Both experimental and computational results revealed that the reaction outcomes in the cases of chloride, bromide and iodide were dictated by product stability through thermodynamic control involving rearrangement of the initially formed primary halides to the more stable secondary halides. The ring opening of the same aziridinium salts with fluoride, however, was shown to be mediated by steric interactions (kinetic control), with the corresponding primary β-fluoro amines being obtained as the main reaction products. Only for 2-acylaziridinium ions was the reaction outcome shown to be under full substrate control, affording secondary β-fluoro, β-chloro, β-bromo and β-iodo amines through exclusive attack at the activated α-carbonyl carbon atom.".
- aggregation authorList BK426796.
- aggregation endPage "4931".
- aggregation issue "25".
- aggregation startPage "4920".
- aggregation volume "2010".
- aggregation aggregates 4133566.
- aggregation aggregates 4133567.
- aggregation isDescribedBy 1028905.
- aggregation similarTo ejoc.201000486.
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