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1 article(s) from Fukuda, Takeshi

A new intermediate in the Prins reaction

Shinichi Yamabe,
Takeshi Fukuda and
Shoko Yamazaki

Beilstein J. Org. Chem. 2013, 9, 476–485, doi:10.3762/bjoc.9.51

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Graphical Abstract

Scheme 1: A general scheme of the Prins reaction.

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Scheme 2: An example of the Prins reaction [4]. The product yields (%) are based on formaldehyde.

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Scheme 3: An equilibrium in the hydrolysis of the product, 1,3-dioxane.

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Scheme 4: Formation of the acetate of an allylic alcohol by Prins reaction [5].

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Scheme 5: A reaction mechanism involving the carbonium-ion intermediate X.

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Scheme 6: A reaction model composed of RHC=CH₂, (H₂C=O)₂ and H₃O⁺(H₂O)₁₃ to obtain the path of step 2 (Scheme 5). H₃O⁺...

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Figure 1: Geometries of the precursor and the transition states (TSs) of the Prins reaction of propene with (...

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Figure 2: Energy changes (in kcal/mol) of the propene Prins reaction calculated by B3LYP/6-311+G(d,p) SCRF=(P...

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Figure 3: Geometries of the transition states (TSs) of the Prins reaction of styrene + (formaldehyde)₂ + H₃O⁺...

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Figure 4: Energy changes (in kcal/mol) of the styrene Prins reaction calculated by B3LYP/6-311+G(d,p) SCRF = ...

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Figure 5: TS1(Ph) geometries of n = 20 and n = 30 in the reacting system of styrene + H₃O⁺(H₂O)_n + (H₂C=O)₂ c...

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Scheme 7: Summary of the present calculated results. The ether in the box is the new intermediate found in th...

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Published 05 Mar 2013

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