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Structures of carbanions, II. Effects of cation, concentration and solvent upon the geometries of reactions of enolate anions

✍ Scribed by Bernard Miller; Howard Margulies; Thomas Drabb Jr.; Richard Wayne

Book ID
104249304
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
198 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the preceding paper' we reported that 0-phosphorylation of the potassium enolatee of a variety of substituted ketones gave mixtures consisting predaainantly of cis-isomers2 from re-action in non-polar solvents and predominantly of trans-isomers 2 from reaction in polar solvents.

Formation of cis-isomers in non-polar solvents could be attributed either to interaction of the negatively charged oxygen with the polar group (-CN, -COnEt, -CoCHs, or -PO(OEt)2), as in StNCtare I, or to chelation of the anion with the potassium cation, a8 in structure II. In either

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## Monohalomalonate carbanions, generated by the 2e-reduction of X,C(CO,Et),(X = Cl or Br) react with Michael acceptors, giving cyclocondensation products (cyclopropane or dihydrofurane derivatives). The chloro carbanion appears to be more reactive; the reactivity of the bromo carbanion strongly d