TY - JOUR
T1 - Vinyl carbanions. Part 3. The reaction of ββ- diphenylacrylonitrile derivatives with butyl-lithium
AU - Melamed, Uri
AU - Feit, Ben A.
PY - 1978
Y1 - 1978
N2 - ββ-Diphenylacrylonitrile (I) reacts with butyl-lithium in THF at -78° to give the derived vinyl carbanion Ph2C=C̄-CN (Ia) in a rapidly established equilibrium. A competing nucleophilic addition of a butyl carbanion at the less hindered α-position, afforded the substituted olefins Ph2C-CHBu and Ph2C=C(Bu)CN, by elimination of either CN- or H-, respectively, from the intermediate carbanion. An addition product of butyl-lithium to (I) was not formed. Reactions of butyl-lithium with trans-α-cyanostilbene and with triphenylacrylonitrile were also carried out in THF at -78° in order to study the effect of structural variations on the site of the nucleophilic attack and on the type of products obtained.
AB - ββ-Diphenylacrylonitrile (I) reacts with butyl-lithium in THF at -78° to give the derived vinyl carbanion Ph2C=C̄-CN (Ia) in a rapidly established equilibrium. A competing nucleophilic addition of a butyl carbanion at the less hindered α-position, afforded the substituted olefins Ph2C-CHBu and Ph2C=C(Bu)CN, by elimination of either CN- or H-, respectively, from the intermediate carbanion. An addition product of butyl-lithium to (I) was not formed. Reactions of butyl-lithium with trans-α-cyanostilbene and with triphenylacrylonitrile were also carried out in THF at -78° in order to study the effect of structural variations on the site of the nucleophilic attack and on the type of products obtained.
UR - http://www.scopus.com/inward/record.url?scp=37049109070&partnerID=8YFLogxK
U2 - 10.1039/p19780001228
DO - 10.1039/p19780001228
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AN - SCOPUS:37049109070
SN - 1472-7781
SP - 1228
EP - 1232
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 10
ER -