29839-61-0

Upstream product

• 4715-17-7 2,2-pentamethylene-4-methylene-1,3-dioxolane 
• 36399-24-3 1-(oxiran-2-ylmethyl)cyclohexan-1-ol 
• 4423-79-4 cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 108-94-1 cyclohexanone 
• 55862-21-0 (±)-4-cyclohexyl-1,2,4-butanetriol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1123-34-8 1-allyl-1-cyclohexanol 
• 55862-16-3 1-oxaspiro<4.5>decan-3-one 

Relevant academic research and scientific papers

Synthesis of tetrahydrofurans by regio- and stereoselective cyclization of epoxyalcohols using magnesium halide

A novel synthetic method for several tetrahydrofuran derivatives by intramolecular cyclization of epoxyalcohols is described. The presence of a catalytic amount of magnesium halide altered the regio- and stereoselectivity of the cyclization reaction.

Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols

Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (ΔA-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields.

General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carbo- and heterocyclic fragments

Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones. Pleiades Publishing, Ltd., 2011.

Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4

Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generat