In:
Helvetica Chimica Acta, Wiley, Vol. 60, No. 5 ( 1977-07-13), p. 1730-1738
Abstract:
( 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.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19770600527
Language:
English
Publisher:
Wiley
Publication Date:
1977
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
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