Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-Iodo-2-methylbutane, is researched, Molecular C5H11I, CAS is 616-14-8, about Secondary to normal alkyl group rearrangements in octahedral iridium(III) complexes. 1. Monoalkyl derivatives.Computed Properties of C5H11I.
sec-Alkyliridium(III) complexes IrYIR(CO)L2 (R = sec-alkyl; Y = Cl, I; L = PMe3, PMe2Ph), formed by oxidative addition of sec-alkyl iodides to IrY(CO)L2, rearrange cleanly by a first-order process to the n-alkyl isomers on dissolution in CH2Cl2 containing protic solvents. The order of efficacy of these solvents in promoting alkyl group rearrangement is CF3CO2H >> CH3OH >> C2H5OH > CH3CO2H ∼ PrOH > (CH3)2CHOH, while in the more strongly coordinating medium of THF the order is H2O >> CH3OH. These orders correlate with the anion-solvating ability of the solvents and, together with the observed retardation by added iodide ion, suggest that the rate-determining step in the rearrangement is dissociation of iodide ion trans to the sec-alkyl group. Rapid, reversible β-hydride elimination in the resulting cation and stereospecific return of iodide ion trans to the resulting n-alkyl group complete the process. The rearrangement is promoted by increasing bulk, both of the alkyl group, up to a certain limit, and of the tertiary phosphine (PMe2Ph > PMe3). Treatment of IrClI{CH(CH3)2}(CO)(PMe2Ph)2 with AgBF4 in MeCN induces immediate alkyl group rearrangement to give the n-propyliridium(III) salt [IrClPr(CO)(NCMe)(PMe2Ph)2]BF4. Studies of analogous CD2CH3 compounds suggest that they, and presumably other n-alkyliridium(III) complexes, undergo reversible β-hydride elimination more slowly than the sec-alkyl complexes. The D labels in the isobutyl-d2 complex IrClI{CD2CH(CH3)2}(CO)(PMe3)2 scramble over all the alkyl C atoms when the compound is heated in CD2Cl2/CD3OD, indicating that a tert-butyliridium(III) species is accessible. Surprisingly, the complexes IrClI{CH2CH(CH3)CH2CH3}(CO)(PMe3)2 and IrClI{CH2CH2CH(CH3)2}(CO)(PMe3)2 do not interconvert under the same conditions, implying that a tert-pentylirdium(III) species cannot be formed. The results are compared with alkyl group rearrangements that occur in other transition-metal systems, especially those promoted by dissociation of Ph3P in (η-C5H5)FeR(CO)(PPh3).
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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem