TY - JOUR
T1 - Vinyl carbanions. Part I. Kinetics of hydrogen-deuterium exchange in fluoren-9-ylideneacetonitrile catalysed by sodium ethoxide
AU - Feit, B. A.
AU - Bohor, L.
AU - Rubinraut, S.
PY - 1976
Y1 - 1976
N2 - The kinetics of hydrogen-deuterium exchange in fluoren-9- ylideneacetonitrile in ethyl [2H] alcohol, catalysed by sodium ethoxide, have been studied. The observed rate equation is (i) where k ex = 1.15 ±0.05 I mol-1 min-1 at R = kex[Olefin][EtO-Na+] (i) 30°. N.m.r. did not show any formation of the addition product of ethyl alcohol to this olefin. Hydrogen-deuterium exchange of the cis- and trans-isomers of 3-(2-bromophenyl)-3-phenylacrylonitrile, under comparable conditions, occurs without any isomerization. It is suggested, therefore, that exchange takes place via the derived vinyl carbanion and not by an addition-elimination mechanism.
AB - The kinetics of hydrogen-deuterium exchange in fluoren-9- ylideneacetonitrile in ethyl [2H] alcohol, catalysed by sodium ethoxide, have been studied. The observed rate equation is (i) where k ex = 1.15 ±0.05 I mol-1 min-1 at R = kex[Olefin][EtO-Na+] (i) 30°. N.m.r. did not show any formation of the addition product of ethyl alcohol to this olefin. Hydrogen-deuterium exchange of the cis- and trans-isomers of 3-(2-bromophenyl)-3-phenylacrylonitrile, under comparable conditions, occurs without any isomerization. It is suggested, therefore, that exchange takes place via the derived vinyl carbanion and not by an addition-elimination mechanism.
UR - http://www.scopus.com/inward/record.url?scp=0346674108&partnerID=8YFLogxK
U2 - 10.1039/P29760000253
DO - 10.1039/P29760000253
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AN - SCOPUS:0346674108
SN - 1472-779X
SP - 253
EP - 256
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 3
ER -