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Synthesis 1977; 1977(10): 661-672
DOI: 10.1055/s-1977-24523
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The Prins Reaction

David R. ADAMS* , Surendra P. BHATNAGAR
  • *The Chemistry Department, The University, Southampton, England
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Publication Date:
04 April 2002 (online)

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The acid-catalysed olefin-aldehyde condensation, known as the Prins reaction, is briefly reviewed in order to present some of the more important aspects of this synthetically useful reaction. This reaction can be used to prepare 1,3-dioxanes, 1,3-glycols, unsaturated alcohols, diolefins, or chloroethers from simple olefins and formaldehyde in the presence of an acid. Reactions of hetero-substituted olefins lead to the correspondingly substituted 1,3-dioxanes, unsaturated acids or esters, or dihydropyrans. Reactions of diolefins lead to product mixtures, depending on the reaction conditions. 1. Reaction of Simple Olefins 1.1. Preparation of 1,3-Dioxanes 1.2. Preparation of 1,3-Glycols, Unsaturated Alcohols, and Diolefins 1.3. Preparation of Chloroethers 2. Reaction of Substituted Olefins 2.1. Reaction of Aryl-Substituted Olefins 2.2. Reaction of Halogen-Substituted Olefins 2.3. Reaction of Hydroxy-Substituted Olefins 2.4. Reaction of Terpenes and Cyclic Olefins 3. Reaction of Dienes