ISSN:
0009-2940
Keywords:
Iron, organo complexes
;
Cobalt, organo complexes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Alkyliron and Alkylcobalt Reagents, VII[1]. - On the Substitution of the Halogen of Alkenyl Chlorides, Alkenyl Fluorides, and Alkynyl Halides by Reagents of the Type R4MLi2 (M=Fe, Co)Me4FeLi2 and Me4CoLi2, which are favourable reagents for the substitution of Br in alkenyl bromides[1-4], also proved to be favourable for the substitution of the halogen in alkenyl chlorides (yields 68-99%; nearly complete retention of configuration in the case of Me4FeLi2), β1-fluorostyrene (best yield 92%), and 1-fluoronaphthalene (best yield 47%). Me4FeLi2 differentiates between various alkenyl chlorides in 1:1 competition experiments better than Me4CoLi2 and is the optimal reagent for the substitution of halogen in 1-chloro-2-phenylethyne (12), 1-bromo-2-phenylethyne (13), and 1-chloro-3-phenoxypropyne (15) by methyl (yields 70, 46, and 80%, respectively). Substitution of the halogen in 12 by the n1-butyl, n1-octyl, and phenyl residue is better achieved by the catalytic systems RMgBr + 2.5 mol % FeCl2 (R=nBu, nOct, Ph; yields 75, 63, and 96%, respectively) than by the reagents nBu4FeLi2, nBu4Fe(MgBr)2, nOct4Fe(MgBr)2, or Ph4Fe(MgBr)2 (yields 18-28%).
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260627
