Stereoaspects of the Prins Reaction of Anethole

Philip S. Portoghese, Edward E. Smissman

Research output: Contribution to journalArticle

6 Citations (Scopus)

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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Stereochemistry
Formaldehyde
Condensation
Hydrogen bonds
Ions
1,4-dioxane
anethole

Cite this

Stereoaspects of the Prins Reaction of Anethole. / Portoghese, Philip S.; Smissman, Edward E.

In: Journal of Organic Chemistry, Vol. 27, No. 3, 01.03.1962, p. 719-722.

Research output: Contribution to journalArticle

Portoghese, Philip S. ; Smissman, Edward E. / Stereoaspects of the Prins Reaction of Anethole. In: Journal of Organic Chemistry. 1962 ; Vol. 27, No. 3. pp. 719-722.
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