[reaction: see text] Rhodium-catalyzed tandem hydroformylation/acetalization of alpha,omega-alkenediols gives facile access to perhydrofuro[2,3b]furans and perhydrofuro[2,3b]pyrans in good yields. Similarly, benzoannelated tetrahydrofuro[2,3b]furans are obtained by hydroformylation of o-hydroxy cinnamyl alcohols.
2‐Butanone is the second most important commercially produced ketone after acetone. It is produced primarily by dehydrogenation of 2‐butanol. 2‐Butanone is used as a solvent in paints and adhesives and shows increasing demand. As a low‐boiling solvent with low viscosity, high solids concentration, and wide diluents' tolerance, 2‐butanone has wide application in polymer industry, where it is considered as a strong competitor to ethyl acetate. In the chemical industry, 2‐butanone can be used as an activator for oxidative reactions, as extractive agent, solvent, and as a chemical intermediate. In 2005, it was removed from the list of hazardous air pollutants. The article contains sections titled: 1. Introduction 2. Physical Properties 3. Chemical Properties 4. Production 4.1. Catalytic Dehydrogenation of sec ‐Butyl Alcohol (SBA) in the Gaseous Phase 4.2. MEK as a Byproduct of the Fischer‐Tropsch Coal‐to‐Liquid Process 4.3. Liquid‐Phase Oxidation of n ‐Butane 4.4. Oxidation of sec ‐Butylbenzene According to the Hock Phenol Synthesis 4.5. Direct Oxidation of n ‐Butenes (Hoechst‐Wacker Process) 5. Quality, Storage, Transportation 6. Uses 7. Economic Aspects 8. Toxicology and Occupational Health 8.1. Occupational Exposure 8.2. Toxicokinetics and Metabolism 8.2.1. Absorption 8.2.1.1 Oral Exposure 8.2.1.2. Inhalation Exposure 8.2.1.3. Dermal Exposure 8.2.2. Distribution 8.2.3. Metabolism 8.2.4. Elimination and Excretion 8.2.5. Mechanism of Action 8.2.6. Toxic Effects 8.2.6.1. Oral Exposure 8.2.6.2. Inhalation Exposure 8.2.6.3. Occupational Health 8.2.6.4. Regulations
Di- or tetrahydropyrans with a vinyl side chain are obtained by diastereoselective ring-closing metathesis or by addition of vinylmagnesium chloride to an appropriately functionalized tetrahydropyranone. The resulting allylic alcohols are converted to spirocyclic hemiacetals under hydroformylation conditions. Oxidation yields the corresponding lactones.
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