TY - JOUR
T1 - Alkylation reactions with organometallic reagents. III. The effect of oxygen on alkylation reactions with cobalt(I) compounds
AU - Michman, M.
AU - Steinberger, B.
AU - Gershoni, S.
PY - 1976/6/29
Y1 - 1976/6/29
N2 - Methylmagnesium bromide reacts with diphenylacetylene in the presence of cobalt(I) and cobalt(II) complexes. Oxygen is shown to have a significant effect on the reaction. Under argon the alkyne is consumed either by formation of cyclisation products or by addition across the triple bond to yield stilbene derivatives and 1,2-diphenylpropene (by mono-alkylation of the triple bond). Under oxygen the consumption of the alkyne through condensation tends to be blocked while the yield of addition reactions to the triple bond increases and includes the formation of 2,3-diphenylbut-2-ene (by dialkylation of the alkyne). The same effect to a smaller extent is observed when CH3Co(Ph3P)3 reacts with PhCCPh. An attempt to rationalize the oxygen effect is presented.
AB - Methylmagnesium bromide reacts with diphenylacetylene in the presence of cobalt(I) and cobalt(II) complexes. Oxygen is shown to have a significant effect on the reaction. Under argon the alkyne is consumed either by formation of cyclisation products or by addition across the triple bond to yield stilbene derivatives and 1,2-diphenylpropene (by mono-alkylation of the triple bond). Under oxygen the consumption of the alkyne through condensation tends to be blocked while the yield of addition reactions to the triple bond increases and includes the formation of 2,3-diphenylbut-2-ene (by dialkylation of the alkyne). The same effect to a smaller extent is observed when CH3Co(Ph3P)3 reacts with PhCCPh. An attempt to rationalize the oxygen effect is presented.
UR - http://www.scopus.com/inward/record.url?scp=0042251269&partnerID=8YFLogxK
U2 - 10.1016/S0022-328X(00)87338-6
DO - 10.1016/S0022-328X(00)87338-6
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AN - SCOPUS:0042251269
SN - 0022-328X
VL - 113
SP - 293
EP - 302
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
IS - 3
ER -