Interaction of Undecenoic Acid with Formaldehyde in Trifluoroacetic Acid.-Prins reaction of undecenoic acid (I) with formaldehyde in the presence of trifluoroacetic acid affords a mixture of trans-(III) and cis-carboxyoctylfuranols (IV) while dioxane or pyranol derivatives, previously obtained in the analogous reaction in sulfuric acid, are not observed. Quantumchemical calculations on the expected cationic intermediates are used to explain this chemoselectivity. -(TALIPOV, R. F.; YUSUPOV, Z. A.; SAFAROV, I. M.; TALIPOVA, R. G.; MUSLUKHOV, R. R.; Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 41 (1998) 4, 131-132; Nauchn.-issled. inst. tonkoi org. sint., Bash. gos. univ., Russia; RU)
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Single-Stage Synthesis of Tetrahydrofuran-3-ol Esters.-The acid-catalyzed reaction of allyl carboxylates (I) with paraformaldehyde is studied. For allyl acetate (Ia) it is shown that dioxane derivative (IV) is formed as a primary adduct due to reaction of allyl derivative with formaldehyde dimers. The content of formaldehyde monomers increases during the reaction providing access to tetrahydrofuran derivatives (III). The reaction is successfully applied to several allyl carboxylates furnishing tetrahydrofuran derivatives (III) [except allyl valerate (Ic) which exclusively affords the dioxane derivative] in moderate yields. -(TALIPOV, R. F.; GAISIN, A. M.; RAMAZANOV, I. R.; YUSUPOV, Z. A.; SAFAROV, M. G.; Izv. Vyssh. Uchebn. Zaved., Khim.
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