TY - JOUR
T1 - On a mechanism for the trans-addition of alkylmagnesium and alkylrhodium derivatives to diphenylacetylene
AU - Michman, Michael
AU - Weksler-Nussbaum, Sophia
PY - 1978
Y1 - 1978
N2 - The reaction of diphenylacetylene with tris(triphenylphosphine)rhodium bromide yields 1,2-diphenylpropene mostly as the trans-isomer. When reactions are terminated with D2O it is shown that trans-1,2-diphenylpropene is deuteriated at the vinylic position and at the ortho-position of the aromatic ring adjacent to the methyl group. The cis-isomer is deuteriated at the vinylic position only. These results offer an explanation of the mechanism of trans-addition in this case. Possible implications for other cases of trans-addition are discussed.
AB - The reaction of diphenylacetylene with tris(triphenylphosphine)rhodium bromide yields 1,2-diphenylpropene mostly as the trans-isomer. When reactions are terminated with D2O it is shown that trans-1,2-diphenylpropene is deuteriated at the vinylic position and at the ortho-position of the aromatic ring adjacent to the methyl group. The cis-isomer is deuteriated at the vinylic position only. These results offer an explanation of the mechanism of trans-addition in this case. Possible implications for other cases of trans-addition are discussed.
UR - http://www.scopus.com/inward/record.url?scp=37049100201&partnerID=8YFLogxK
U2 - 10.1039/p29780000872
DO - 10.1039/p29780000872
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AN - SCOPUS:37049100201
SN - 1472-779X
SP - 872
EP - 875
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 9
ER -