- Tuning the reducing properties of 1,2-diaryl-1,2-disodiumethanes
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(Chemical Equation Presented) We investigated the reducing properties of a series of 1,2-diaryl-1,2-disodiumethanes by means of equilibration reactions. The electron-donor power of these vic-diorganometals is strongly affected by the nature of substituents present either on the aromatic ring(s) or on the carbanionic centers, and it can be correlated with their ability to delocalize the arylmethyl carbanions. These findings are supported by electrochemical analysis of the reduction behavior of the parent 1,2-diarylalkene. Applications of these results to the reduction of selected substrates are described. 2009 American Chemical Society.
- Azzena, Ugo,Pisano, Luisa,Antonello, Sabrina,Maran, Flavio
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supporting information; experimental part
p. 8064 - 8070
(2010/03/02)
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- Improved synthesis of C2-symmetrical pyridinediols and synthesis of C(s)-symmetrical pyridinediols
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Base-induced reaction of 2,6-dimethylpyridine (2,6-lutidine) (1) with two equivalents of various ketones has been reported to provide C2-symmetrical pyridine diols 3. Closer examination reveals that competitive di-addition to a single methyl gr
- Koning, Bartjan,Buter, Jan,Hulst, Ron,Stroetinga, Roelof,Kellogg, Richard M.
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p. 2735 - 2743
(2007/10/03)
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- DIPHENYLHYDROXYMETHYLATION OF 2-METHYLPYRIDINE N-OXIDE BY KETYLS AND DIANIONS OF BENZOPHENONE
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In the reaction of 2-methylpyridine N-oxide with the lithium ketyl and the dianion of benzophenone the products from diphenylhydroxymethylation in the side chain, i.e., 2-(1-hydroxy-1,1-diphenylethyl)pyridine N-oxide, and in the ring, i.e., 2-methyl-6-(diphenylhydroxymethyl)pyridine N-oxide, are formed.The product from reductive diphenylhydroxymethylation in the methyl group, i.e., 2-(1-hydroxy-1,1-diphenylethyl)pyridine, is formed preferentially in the reactions with the ketyl and the dianion of benzophenone.The condensation with the sodium ketyl and the dianion of benzophenone takes place similarly and leads to significantly lower yields of the products.
- Kurbatova, A. S.,Kurbatov, Yu. V.,Niyazova, D. A.,Atayan, P. S.
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p. 168 - 170
(2007/10/02)
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