1967
DOI: 10.1139/v67-351
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Addition of alkoxide ions to alkenes. The HR– scale

Abstract: By using α-cyanostilbenes as Lewis acids, Lewis acidity scales have been established in ethanolic and methanolic dimethyl sulfoxide containing the appropriate 0.01 M sodium alkoxide and in the system sodium methoxide – methanol. This scale, designated [Formula: see text], describes the ability of the solvent to add an alkoxide ion to an alkene. The [Formula: see text] values range from 11.73 in methanol to 21.74 in 93.27 mole % dimethyl sulfoxide in ethanol.The most acidic indicator used to establish the sca… Show more

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Cited by 22 publications
(5 citation statements)
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“…In contrast, the reactions of the benzylidene malonates 3m − u with the carbanions 1b , c in methanol resulted in the formation of α-cyano stilbenes 6bm − 6cu via Michael addition, proton shift, and retro-Michael addition (eq ). Compounds 6 were previously employed for the determination of H R -acidity scales …”
Section: Resultsmentioning
confidence: 99%
“…In contrast, the reactions of the benzylidene malonates 3m − u with the carbanions 1b , c in methanol resulted in the formation of α-cyano stilbenes 6bm − 6cu via Michael addition, proton shift, and retro-Michael addition (eq ). Compounds 6 were previously employed for the determination of H R -acidity scales …”
Section: Resultsmentioning
confidence: 99%
“…From the similarity between the U.V. spectra of the products formed from a-cyano-4-nitro-4'-X-stilbenes and those of the anion of 4-nitrophenylacetonitrile (5), and the 1 'Killam Postdoctoral Fellow. =Address as of August 1, 1969, Department of Chemistry, University of Guelph, Guelph, Ontario.…”
Section: Introductionmentioning
confidence: 99%
“…1 ; X is an electronegative sustituent) (1). The existence of species of type 1 has been verified in the case of substituted stilbenes for charged nucleophiles (2)(3)(4).…”
mentioning
confidence: 88%