Stereochemistry of base-catalyzed double-bond migration in allyl ethers

H. Kloosterziel, J.A.A. Drunen, van

Research output: Contribution to journalArticleAcademicpeer-review

25 Citations (Scopus)


Base-catalyzed isomerization of trans-3-methoxy-1-phenylpropene yields stereospecifically as the initial product cis-1-methoxy-3-phenylpropene. This is caused by the (intermediate) formation of the cis-1-methoxy-trans-3-phenylallyl anion (I), which is energetically favored over the trans-isomeric anion (II). The NMR spectra of I and II are described. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)32-36
JournalRecueil des Travaux Chimiques des Pays-Bas
Issue number1
Publication statusPublished - 1970


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