Decanone

In a lOOmL round-bottomed flask fitted with a magnetic stirrer is placed a mixture of palladium (II) chloride (89mg, O.Smmol), p-benzoquinone (5.94g, 55mmol) and 7 1 dimethylformamide/water (20mL). To the solution, t-decene [substitute safrole for this compound) (7.0g, 50mmc4) is added in 10 min and the mixture is stirred at room temperature for 7h. The solution is poured into cold 3 normal hydrochloric acid (lOOmL) and extracted with 5 portions of ether. The extracts are combined and washed with three portions of 10% aqueous sodium hydroxide solution and a portion of brine, and then dried After removal of the solvent, the residue is distilled to give 2-decanone [P2P] yield 6.1g (78%). 

In contrast to oxidation in water, it has been found that 1-alkenes are directly oxidized with molecular oxygen in anhydrous, aprotic solvents, when a catalyst system of PdCl2(MeCN)2 and CuCl is used together with HMPA. In the absence of HMPA, no reaction takes place(100]. In the oxidation of 1-decene, the Oj uptake correlates with the amount of 2-decanone formed, and up to 0.5 mol of O2 is consumed for the production of 1 mol of the ketone. This result shows that both O atoms of molecular oxygen are incorporated into the product, and a bimetallic Pd(II) hydroperoxide coupled with a Cu salt is involved in oxidation of this type, and that the well known redox catalysis of PdXi and CuX is not always operalive[10 ]. The oxidation under anhydrous conditions is unique in terms of the regioselective formation of aldehyde 59 from X-allyl-A -methylbenzamide (58), whereas the use of aqueous DME results in the predominant formation of the methyl ketone 60. Similar results are obtained with allylic acetates and allylic carbonates[102]. The complete reversal of the regioselectivity in PdCli-catalyzed oxidation of alkenes is remarkable. 

A GENERAL SYNTHETIC KTHQO FOR THE PREPARATION OF ICTHYL KETONES FROM TERMINAL OLEFINS 2-DECANONE... 

The metal-catalysed autoxidation of alkenes to produce ketones (Wacker reaction) is promoted by the presence of quaternary ammonium salts [14]. For example, using copper(II) chloride and palladium(II) chloride in benzene in the presence of cetyltrimethylammonium bromide, 1-decene is converted into 2-decanone (73%), 1,7-octadiene into 2,7-octadione (77%) and vinylcyclohexane into cyclo-hexylethanone (22%). Benzyltriethylammonium chloride and tetra-n-butylammo-nium hydrogen sulphate are ineffective catalysts. It has been suggested that the process is not micellar, although the catalysts have the characteristics of those which produce micelles. The Wacker reaction is also catalysed by rhodium and ruthenium salts in the presence of a quaternary ammonium salt. Generally, however, the yields are lower than those obtained using the palladium catalyst and, frequently, several oxidation products are obtained from each reaction [15]. 

The ruthenium complex of 49 was chosen due to its easy accessibility and because preliminary experiments had shown that simple non-prochiral aliphatic ketones such as 4-methyl-cyclohexanone are quantitatively reduced. This positive outcome encouraged us to test various prochiral aliphatic ketones 64-75. The results using standard conditions are summarized in Fig. 23. Most substrates could be reduced in good yields and the enantioselectivities of six alcoholic products are higher than 85%, 2-decanone 67 and geranylacetone 68 showed even ee s of 95%, demonstrating that the concept works well not only for aromatic ketones. 

CASRN 693-54-9 molecular formula C10H20O FW 156.27 Biological. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM 2-decanone) and ThOD were 6.97 and 48.1%, respectively (Vaishnav et al., 1987). 

Similar results were obtained in the biphasic Wacker oxidation of 1-decene, catalyzed by PdS04, CUSO4 and a heteropolyacid H9PV6M06O40 in the presence of chemically modified p-cyclodextrins (methyl, methoxy, hydroxypropyl derivatives). The reactions yielded 2-decanone in rather high yield (up to 58 %) accompanied by extensive isomerization of 1-decene to internal decenes. Nevertheless, these latter apparently did not react, since the ratio of 2-decanone among the oxodecenes exceeded 99 % (Scheme 10.12). 

Addition to a-aikoxy carbonyl compounds. n-Butylmagncsium bromide reacts stercosclcctivcly with protected, chiral a-hydroxy ketones. For example, reaction of the Grignard reagent with the MEM ether of 3-hydroxy-2-decanone in THF leads to the f/ireo-product [>95% isolated yield (equation I)]. The stereoselectivity is much lower when n-butyllilhium is used in addition the solvent plays an important role. Stereoselectivity is lower in C5H, 2, CH2CI2, and ether. A number of protective... 

Tetradecane 2-Decanone Octanoic acid 5-Heptyldihydro-2(3H)-furanone... 

Figure 7.9 (a) X-ray diffraction channel oscillation photograph of 2-decanone-urea showing host... 

Bearden, A.P., Gregory, B.W. and Schultz, T.W. (1997) Growth kinetics of preexposed and naive populations of Tetrahymenapyriformis to 2-decanone and acetone, Ecotoxicology and Environmental Safety 37 (3), 245-250. 

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