1 - cycloalkanol cycloalkanone

The derivatives 24 were synthesised by the acylation of trans-2-aminocy-clopentanol (n=l) or frans-2-aminocyclohexanol (n=2) with 3,3-ethylene-dioxydodecanoic acid in the presence of EDC, DMAP and DIPEA followed by acidolysis with THF in DCM. The cycloalkanone analogues 25 were obtained by Swern oxidation of the corresponding cycloalkanols 24 (Scheme 10). 

Interestingly, cyclopentane and cyclohexane derivatives, which contain one or two hydroxyl, carbonyl, or carboxyl groups, degrade more readily in the environment than do their parent compounds. In fact, microorganisms capable of degrading of cycloalkanols and cycloalkanones are ubiquitous in environmental samples. 

Recently, Corma et al. have patented a process of oxidizing cycloalkane with molecular oxygen to produce cycloalkanol and/or cycloalkanone in the presence of hydrotalcite-intercalated heteropoly anion [Co MnCo (H20)039] (M = W or Mo), which comprised one cobalt as a central atom and another as a substitute of a W=0 fragment in the Keggin structure [98]. At 130 °C and 0.5 MPa, 64 and 24% selectivity to cyclohexanone and cyclohexanol, respectively, was achieved at cyclohexane conversion about 5%. This catalytic system could be of practical importance provided a true heterogeneous nature of catalysis and good catalyst recyclability had been proved. Unfortunately, this information was lacking in [98]. 

These products are stable when stored at 50°, can be poured at temps below 100°, and have high deton velocities. The expls can be used alone, mixed with one another, or mixed with other expls (Ref 2). Kincaid McGill (Ref 4) found that the polynitrate esters of poly(hydroxy-methyl) cycloalkanones and of poly(hydroxy-methyl) cycloalkanols are capable of plasticizing NC. They describe a flashless, nonhygio-scopic propint (NGu, NC plasticizer) which is reported superior to proplnts plasticized with a volatile HE. Derivatives of cycloalkanone which have therapeutic value were prepd by Ritzer (Ref 6)... 

The kinetics of the potassium hexacyanoferrate(III)-catalysed oxidation of glucose with ammonium peroxodisulfate have been studied.82 The kinetics and mechanism of oxidation of some cycloalkanols by alkaline Fe(CN) have been reported.83 The same group has also studied the oxidation of cycloalkanones under comparable conditions and determined the order of reactivity as cyclohexanone > cyclopentanone > cyclo-octanone > cycloheptanone.84 Palladium(II) has been found to catalyse the oxidation of formaldehyde, thiourea, and thioacetamide by alkaline Fe(CN)g, whereas no effect is observed in the oxidation of acetaldehyde.85 The orders of reaction have been determined and a mechanism was proposed. 

Acyclic polycarboxylic acids, e.g., from cycloalkanols and/or cycloalkanones Saturated lower fatty acids, general... 

Greater preparative importance attaches to oxidative ring opening of cycloalkanols and cycloalkanones, which then afford alkanedioic acids containing an unchanged number of carbon atoms. Thus, for instance, adipic acid is obtained in up to 90% yield from cyclohexanol or cyclohexanone by means of about 60% nitric acid containing vanadium and copper salts as catalyst 125... 

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