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Stereochemie und Mechanismus derPrins-Reaktion bei ausgeprägter Ladungsdelokalisierung im intermediären Carbeniumion

Stereochemistry and mechanism of the prins reaction involving strong charge-delocalization in the intermediate carbenium ion

  • Organische Chemie und Biochemie
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Abstract

A detailed investigation of the reaction of 2.6-dimethyl-4-propenylphenol with formaldehyde showed thatPrins reactions of hydroxystyrenes in alkaline medium in most cases are kinetically controlled. By attack of formaldehyde, the same intermediate is generated from eithercis ortrans olefin. On further reaction by two independent pathways a 1.3-diol is formed by attack of a hydroxyl ion, or a 1.3-dioxane by reaction with additional formaldehyde via a hemiacetal. The steric course of the reaction is deduced from a discussion of the conformations of transition states.Prins reactions of arylolefins carrying strong +M-substituents proceed analogously under acylating conditions (e.g. in acetic acid) in weak acidic medium.

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  1. Institut für Organische Chemie und Organisch-chemische Technologie der Technischen Hochschule Graz, Österreich

    H. Griengl & W. Sieber

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  1. H. Griengl
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Griengl, H., Sieber, W. Stereochemie und Mechanismus derPrins-Reaktion bei ausgeprägter Ladungsdelokalisierung im intermediären Carbeniumion. Monatshefte für Chemie 104, 1008–1026 (1973). https://doi.org/10.1007/BF00903917

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