Steric Requirements in Base-Promoted Elimination Reactions

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概要

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• The effect of the steric requirement of the attacking base in base-promoted elimination reactions was studied using a variety of pairs of diastereoisomeric bases. The pairs of diastereoisomeric alkoxide bases examined gave difinitely different <I>cis</I>-olefin to <I>trans</I>-olefin ratios from elimination reactions of secondary alkyl bromides and tosylates in dimethyl sulfoxide. The results indicate unambiguously that the steric requirement of the attacking base is an important controlling factor in determining the olefinic product distribution in these elimination reactions. The structural effect of the solvent molecule was also investigated using pairs of diastereoisomeric alcohols in base-promoted elimination reactions. Under a variety of conditions the effect upon the product distribution observed was rather small, as compared with those observed for the diastereoisomeric bases, to be an important contributing factor on the product distribution.

• 公益社団法人 日本化学会の論文

著者

• Ishizawa Akio

  Department of Chemistry, Faculty of Science, Kyoto University

関連論文

• Long Spacings of ω-Cyclohexyl Alkanols
• Long Spacings of α,ω-Dicyclohexyl Alkanes and α, ω-Diphenyl Alkanes
• Steric Requirements in Base-Promoted Elimination Reactions

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