Prototropic isomerization of isopentene derivatives

Široký, Miroslav; Procházka, M.

doi:10.1135/cccc19782635

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Z-stereoselective Double Bond Migration1

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2006

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“…Besides, many Z-stereoselective double bond migrations in O- [53][54][55], N- [56][57][58], and S- [59] allylic systems were of course described in literature, but they were catalysed by bases. In our opinion, Z-stereoselectivity of the reactions investigated by us results from steric effects (Q = Ph 3 CO, Me 3 CO, Ph 3 CSi, [42,44,48,50,60].…”

Section: Z-stereoselective Double Bond Migrationmentioning

confidence: 98%

The role of the functional group in double bond migration in allylic systems catalysed by ruthenium hydride complexes

Krompiec

Kuźnik

Krompiec

et al. 2006

Journal of Molecular Catalysis A: Chemical

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Section: Z-stereoselective Double Bond Migrationmentioning

confidence: 98%

The role of the functional group in double bond migration in allylic systems catalysed by ruthenium hydride complexes

Krompiec

Kuźnik

Krompiec

et al. 2006

Journal of Molecular Catalysis A: Chemical

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Competing Isomerizations: A Combined Experimental/Theoretical Study of Phenylpentenone Isomerism

et al. 2006

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The possible competition of Z/E versus hydrogen-shift isomerization in (E)-5-phenyl-3-penten-2-one (E-1) and (E)-5-phenyl-4-penten-2-one (E-2) was studied, both experimentally and theoretically. Iodine-catalyzed isomerization experiments and computational modeling studies show that the equilibrated system consists predominantly of E-1 and E-2, with E-2 in moderate excess, and with no detectable amounts of the Z (cis) diastereoisomers. Density functional theory (DFT) calculations corroborated the free energy difference (Delta(r) and Delta(r) were -0.7 and -1.1 kcal mol(-1), respectively), and computations of Boltzmann-weighted (1)H NMR spectra were found to be useful in confirming the assignment of the isomers. The relevance of this equilibrium to earlier work on double-bond stabilization is discussed.

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Prototropic isomerization of isopentene derivatives

Cited by 2 publications

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The role of the functional group in double bond migration in allylic systems catalysed by ruthenium hydride complexes

The role of the functional group in double bond migration in allylic systems catalysed by ruthenium hydride complexes

Competing Isomerizations: A Combined Experimental/Theoretical Study of Phenylpentenone Isomerism

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