Stereoaspects of the Prins Reaction of Anethole

Philip S. Portoghese, Edward E. Smissman

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The stereochemistry of 1-anisyl-2-methyl-1,3-diacetoxypropane diasteromers (Ia, Ib) which arise from the condensation of formaldehyde with anethole has been assigned by the use of conformational principies and intramolecular hydrogen bonding studies. The formation of the above Compounds and 4-anisyl-5-methyl-1,3-dioxane (III) are rationalized as proceeding through a classical carbonium ion intermedíate.

Original languageEnglish (US)
Pages (from-to)719-722
Number of pages4
JournalJournal of Organic Chemistry
Volume27
Issue number3
DOIs
StatePublished - Mar 1 1962

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