Stereoaspects of the Prins Reaction of Anethole

Philip S. Portoghese; Edward E. Smissman

doi:10.1021/jo01050a003

Stereoaspects of the Prins Reaction of Anethole

Philip S. Portoghese, Edward E. Smissman

Medicinal Chemistry

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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 language	English (US)
Pages (from-to)	719-722
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	27
Issue number	3
DOIs	https://doi.org/10.1021/jo01050a003
State	Published - Mar 1 1962

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Stereoaspects of the Prins Reaction of Anethole

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