Decane-1,10-diol

Dimer diola) Dimer diola> 12-Hydroxystearyl alcohol stearyl alcohol Decane-1,10-diol... 

The trifluoroacetates of 1-hexanol and 1-heptanol had retention times of 3.0 and 5.1 minutes, respectively, on Carbowax at 80°C. The trifluoroacetates of 1-undecanol, nonane-1,9-diol, and decane-1,10-diol had retention times of 4.0, 5.1, and 7.6 minutes on Apiezon at 170°C. Peaks were well formed and did not have the characteristic tail of alcohol peaks. The reduction-trifluoroacetylation treatment of 5-ketohexanoic... 

Decan-1,10-diol [112-47-0] M 174.3, m 72.5-74°. Crystd from dry ethylene dichloride. 

Synthesis of 1,10-Decanedialdehyde (12) by Aerobic Oxidation of Decane-1,10-diol, Catalyzed by Pd(ll)-Hydrotalcite [18]... 

Decane 1-10 diol Decane 1-12 diol Decane 1-16 diol... 

One of the earliest rotaxane syntheses involved statistical threading. Harrison and Harrison [4] coupled the 30-membered macrocycle (3) bearing a pendent carboxylic group to a Merrifield s peptide resin, forming the resin adduct (4) (Figure 7). Next, a column was charged with this modified resin and treated with a solution of decane-1, 10-diol (5) and triphenylmethyl chloride (6) in a mixture of pyridine, dimethylfor-mamide and toluene. The process was repeated 70 times. After washing the column,... 

The first mention of synthetic rotaxanes appeared in 1967 [11]. It was based on statistical threading of an immobilized cycle by decane-1,10-diol followed by capping using a trityl ether bulky oup. Another system using statistical threading 1 to rotaxanes in relatively high yield [12]. A directed synthesis was also reported in 1969 by Schill and Zollenkopf.[13]... 

Heomatka and Aub [34] have established for diols a linear relation between the log of the /-value and the number of carbon atoms when using absolute ethanol or dioxan on silica gel G layers they studied ethylene glycol, propane-1,3-diol, hexane-1,6-diol, heptane-1,7-diol, nonane-1,9-diol, decane-1,10-diol and tridecane-1,13-diol. 

Butane-1,4-diol Pentane-1,5-diol Hexane-1,6-diol Decane-1,10-diol Dodecane-1,12-diol Tetradecane-1,14-diol... 

Shigematsu et al. (3) prepared aliphatic polymers containing ketone and ether components in the main chain, (III), by the dehydration of glycerol followed by treatment with 1,10-decane diol and sulfuric acid at 165°C. 

Diols are faster oxidized than the corresponding monoalcohols as the voltammetric-ally determined relative rates have already indicated. In preparative electrolysis 1,10-decane diol is about five times faster oxidized than 1-decanol. 

Physical properties are related to ester-segment structure and concentration in thermoplastic polyether-ester elastomers prepared hy melt transesterification of poly(tetra-methylene ether) glycol with various diols and aromatic diesters. Diols used were 1,4-benzenedimethanol, 1,4-cyclo-hexanedimethanol, and the linear, aliphatic a,m-diols from ethylene glycol to 1,10-decane-diol. Esters used were terephthalate, isophthalate, 4,4 -biphenyldicarboxylate, 2,6-naphthalenedicarboxylate, and m-terphenyl-4,4"-dicarboxyl-ate. Ester-segment structure was found to affect many copolymer properties including ease of synthesis, molecular weight obtained, crystallization rate, elastic recovery, and tensile and tear strengths. 

An imide monomer was synthesised from 4-nitrophthalic anhydride N-(4 -carboxyphenyl)>4-(4 -carboxyphenoxy)phthaHmide. (14). This was reacted (via its dimethyl ester) with chloro- or phenylhydroquinone to form wholly aromatic co-poly(esterimide)s which were found to exhibit a nematic phase in the melt. Similar PEIs derived from aliphatic diols produced only isotropic polymers. Thus, PEI derived from 4-(4 -carboxyphenoxy)phthalimide and n-do-decane diol melted at 162 °C, Tg=66 °C, and was isotropic [28]. The above imide monomer based on phthalic anhydride was therefore shown to be a poor mes-ogen compared with its trimellitic anhydride analogue (4). 

The photo-cured poly(diol-tricarballylate) (PDT) degradable bioelastomers were prepared based on the polycondensation reaction between tricarballylic acid and alkylene diols such as 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol and 1,12-dodecanediol, followed by acrylation and photo-cross-linking, as shown in Scheme 8.29.The PDT prepolymers, such as poly(l,6-hexane diol-co-tricarballylate) (PHT), poly(l,8-octane diol-co-tricarballylate) (POT), poly(l,10-decane diol-co-tricarballylate) (PDET and poly(l,12-dodecane... 

Tetrahydrofiirmi, 1,3-butadiene, CO2, CO, H2O, benzoic acid, terephthahc acid, terephthalic acid mono-3-butenyl, toluene, phenol, benzene CO, CO 2> butadiene, tetrahydrofriran, toluene, benzene, 1,5-hexadiene, dihydrofiiran, 4-vinyl cyclohexene, 1,4-butane (hoi, benzaldehyde, benzoic acid, terephthaldehydic acid, terephthahc acid, mono-3-butenyl terephthalate, cychc dimer, short chain fragments CO, CO2,1,9-decadiene, 1,10-decane diol, 1-decene-lO-ol, benzoic acid, terephthahc acid, mono-decenyl terephthalate Cychc ohgomets, CO, CO 2, acetaldehyde, 2-ethylacrolein CO2, H2O, butadiene, tetrahydrofriran... 

Similarly, androstane-5a,6a,17)S-triol 6-tosylate 17-benzoate (115b) is converted to 17)S-hydroxy-6)S-methyl-10(5 6)SH)flZ)en-androstan-5-one benzoate (116b) on treatment with calcium carbonate in dimethylformamide. Similar treatment of 10-methyldecalin-l,9-diol 1-tosylate (121) gives 10-methylbicyclo[5.3.0]decan-l-one (122). 

Fig. 4. Diagrammatic representation of layered crystal structures of rigid diols, with closed hydrogen bonding cycles. Open circles are oxygen atoms, filled circles hydrogen atoms, and the solid lines represent the connecting diol. Hydrogen bonds are shown as broken lines, (a) The structure of 2,6-dihydroxy-2,6-dimethyltricyclo[3.3.1.13,7]decane (4). (b) The structure of erafo-2,e do-6-dihydroxy-2,6-dimethylbicyclo[3.3.1]nonane, (7)...

A few other oxidations involve no C=C bond cleavage. Cti-9-octadecene gave 9.10-diketo-octadecane with RuO /aq. Na(C10)/( Bu N)Br/CHjCl2 [324], while cyclo-octene was oxidised by RnCyaq. Na(10 )/DCE to 8-oxo-octanal [325]. Oxidation of A -, and A - steroids using RuO /aq. Na(10 )/acetone gave cis-diols, diones and acids [303] while RuO /aq. Na(10 )/CHjCyCH3CN oxidised 2,3-dichlorodecene to decane-2,3-dione [326]. 

In the synthesis of the head-to-head [4 + 4] dimer of cyclopentadiene, the preferential reductive fission of the C3-C4 bond in bishomocubane again plays a significant role.43 Thus, catalytic hydrogenation of bishomocubane-6,10-diol (14) over 10% palladium on charcoal in ethyl acetate at 2.7-3.4 atmospheres for two days furnished the bishomosecocubanediol tetracy-clo[5.2.1.02,< .04 8]decane-5,10-diol (15).43... 

Note. (1) These reaction conditions are used for the oxidation of decan-l-ol, hexane-1, 6-diol and oct-2-yn-l-ol. In the case of alcohols where acid-sensitive groups are also present (e.g. tetrahydropyranyl ethers), sodium acetate is added to buffer the reaction mixture alternatively pyridinium dichromate may be used.99... 

Cobalt(II) salts are effective catalysts for the oxidation of 1,2-glycols with molecular oxygen in aprotic polar solvents such as pyridine, 4-cyanopyridine, benzonitrile, DMF, anisole, chlorobenzene and sulfolane. Water, primary alcohols, fatty acids and nitrobenzene are not suitable as solvents. Aldehydic products are further oxidized under the reaction conditions. Thus, the oxidative fission of rram-cyclo-hexane-l,2-diol gives a mixture of aldehydes and acids. However, the method is of value in the preparation of carboxylic acids from vicinal diols on an industrial scale for example, decane-1,2-diol is cleaved by oxygen, catalyzed by cobalt(II) laurate, to produce nonanoic acid in 70% yield. ... 

In 2006, Yus and co-workers (140) used a similar approach to directly convert 3-methylidenepentane-l,5-diols into l,7-dioxaspiro[4.5]decanes with high yields. The products can then be transformed into other synthetically useful molecules (e.g. lactones) (Fig. 33). 

L)io a-spiro[4.5]decan 6-Brom-E14a/1, 221 (Keton/Diol/Br2)... 

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