ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(Z)-1-Alkylated propenes undergo metallation at an allylic site more rapidly than do their (E)-isomers, no matter in which configuration the resulting organometallic is thermodynamically more stable. A striking illustration is given by (Z)-4,4-dimethyl-2-pentenyl potassium which is formed 15 times faster than its (E)-isomer, although the latter is clearly favored under equilibrium conditions. The configurational reorganization of alkenylpotassium compounds in tetrahydrofuran solution is very slow. At least in one case, however, traces of oxygen efficiently catalyse the Z/E equilibration.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19770600527
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