76785-05-2Relevant academic research and scientific papers
The mechanisms of n-butyllithium induced β-cleavage of 2-methyltetrahydrofuran and oxepane
Cohen, Theodore,Stokes, Stephen
, p. 8023 - 8024 (2007/10/02)
The n-butyllithium induced β-cleavage reactions of 2-methyltetrahydrofuran and oxepane operate via different mechanisms. 2-Methyltetrahydrofuran undergoes an E2 elimination, whilst oxepane undergoes an α,β′-elimination involving initial deprotonation at the α-position followed by a transannular hydrogen transfer.
Does the Dieckmann Condensation Occur in the Gas Phase ?
Raftery, Mark J.,Bowie, John H.
, p. 719 - 722 (2007/10/02)
Burinsky and Cooks have reported that deprotonated dimethyl adipate eliminates methanol via a gas-phase Dieckmann condensation.This is in contrast to the behaviour of simple methyl ester enolates which lose MeOH by a different mechanism, e.g.MeOCOCHCH2R -> -> O=C=CHCHR + MeOH.Evidence is presented which supports the Dieckmann mechanism for adipates.For example, MeOCOC(Me)CH2CH2CD(Me)CO2Me should eliminate MeOD in a Dieckmann condensation, but MeOH by the alternative mechanism outlined above.Experimentally , MeOD is lost exclusively.Similarly, MeOCOCDCH2CH2C(Me)2CO2Me also loses MeOD, consistent with a Dieckmann process
PREPARATION OF CYCLOHEPTANOLS SYMMETRICALLY LABELLED WITH DEUTERIUM
Turecek, Frantisek
, p. 1820 - 1825 (2007/10/02)
Cycloheptanols labelled symmetrically with deuterium in "inaccessible" positions were prepared by multistep syntheses.The key intermediates of the syntheses were the corresponding labelled octanedioic acids.The method of two-phase oxidation of olefins to
