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Prins reaction
The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile.〔''Condensation of formaldehyde with some unsaturated compounds'' H. J. Prins, Chemisch Weekblad, 16, 64, 1072, 1510 1919〕〔Chemical Abstracts 13, 3155 1919〕〔''The Olefin-Aldehyde Condensation. The Prins Reaction''. E. Arundale, L. A. Mikeska Chem. Rev.; 1952; 51(3); 505–555. (Link )〕 The outcome of the reaction depends on reaction conditions (''scheme 1''). With water and a protic acid such as sulfuric acid as the reaction medium and formaldehyde the reaction product is a 1,3-diol. When water is absent, the cationic intermediate loses a proton to give an allylic alcohol. With an excess of formaldehyde and a low reaction temperature the reaction product is a dioxane. When water is replaced by acetic acid the corresponding esters are formed.
==History==
The original reactants employed by Dutch chemist Hendrik Jacobus Prins in his 1919 publication were styrene (''scheme 2''), pinene, camphene, eugenol, isosafrole and anethole.
In 1937 the reaction was investigated as part of a quest for di-olefins to be used in synthetic rubber.
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