ISSN:
0009-2940
Keywords:
Torsional (Z/E) isomerization
;
Selectivity, regio- and stereo-
;
Allylsilanes
;
Allylic oxidation
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Alk-2-enylpotassium compounds having the endo conformation are synthetically very valuable precursors of (Z)-olefinic derivatives substituted at the outward allylic position. They may be generated by „stereoconservative‘ metalation of the readily available (Z)-alk-2-enes by using the superbasic mixture of butyllithium and potassium tert-butoxide or by metalation under similar conditions of stereorandom mixtures of alk-2-enes or alk-1-enes followed by torsional isomerization of the concomitantly formed exo conformers to the thermodynamically more stable endo species. The principal factors that dictate the rate and the extent of the endo/exo equilibration are the substrate geometry, the solvent, the temperature, the reagent stoichiometry, and catalysis.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19971300113
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