Cyclo octene

COT is prepared by the polymerization of ethyne at moderate temperature and pressure in the presence of nickel salts. The molecule is non-planar and behaves as a typical cyclic olefin, having no aromatic properties. It may be catalytically hydrogenated to cyclo-octene, but with Zn and dil. sulphuric acid gives 1,3,6-cyclooclairiene. It reacts with maleic anhydride to give an adduct, m.p. 166 C, derived from the isomeric structure bicyclo-4,2,0-octa-2,4,7-triene(I) ... 

HOaQCHjlfiCOiH, CSH14O4. Important dicarboxylic acid obtained by oxidizing ricino-leic acid (from castor oil) also obtained by oxidation of cyclo-octene or cyclo-octadiene formerly obtained from cork. Used in the formation of alkyd resins and polyamides. Esters are used as plasticizers and heavy duty lubricants and oils. 

Unsubstituted monocyclic mono-olefins, e.g. cyclopentene and cyclo-octene, which yield polypentenamers and polyoctenamers respectively. 

In 1980 the Goodyear company announced copolymers of cyclopentadiene, cyclo-octene or cyclo-octa-1,5-diene with the Diels-Alder addition product of hexachlorocyclopentadiene and cyclo-octa-1,5-diene. This material has been proposed as an alternative to the polychloroprenes, with lower ( 5°C), and superior ozone resistance... 

Fujii, T., and Y. Saito, Thermocatalytic formation of molecular hydrogen and cyclo-octene from cyclo-octane by rhodium complexes. /. Chem. Soc., Chem. Commun., 757-758 (1990). 

Another important feature of this reaction is the synthesis of highly strained E-cycloalkenes. Thus E,Z-cycloocta-1,3-diene has been obtained from the Z,Z-compound in sensitized irradiation 309) (3.4), while E-cyclo-octene was obtained from the Z-isomer by direct irradiation (3.5) 310). The synthesis of a trans doubly bridged olefin has also been reported (3.6)311>. 

C6-C6-C6BiN 5,6,7,12-Tetrahy dro-6-aza-12-bisma-dibenzo [a,d]cyclo-octene... 

Olefinic compounds such as a-pinene (309) and /Dpi none (312) undergo hydrogen abstraction followed by rearrangement and amino-oxyl insertion (310, 313) and addition reactions (311, 314, 315), as shown in reactions 43 and 44627. Other olefinic compounds such as norbomadiene, cyclo-octene and cyclo-octa-1,5-diene gave analogous results628. 

The reaction of [(Tr-C5H5)Mn(CO)3 (CS) j(cyclo-octene)] with CS2 gives good yields of [(7r-C5Hj)Mn(CO)3 (CS)J when x = 1 and 2, and small yields of the trithiocarbonyl complex. ... 

The automatic procedure for reference spectra generation was first demonstrated for the start-up of a homogeneous catalyzed rhodium hydroformylation of cyclo-octene using Rh4(CO)i2 as precursor, n-hexane as solvent and FTIR as the in situ spectroscopy at 298 K [63]. The first n spectra were (i) empty spectrometer compartment (background), (ii) n-hexane at 0.2 MPa in a high pressure thermostatically controlled cell fitted with Cap2 windows (iii) system equilibrated with 2.0 MPa CO, (iv) system upon addition of cyclo-octene, and (v) system upon addition of Rh4(CO)i2. The n=l reference spectrum, which contained atmospheric... 

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]. 

RuCl2(H20) ]+ This species was made from RUCI3 in HCl from pH 0.4-2.0. Kinetic studies suggest that in the epoxidation by [Ru(7l2(H20)4]X02/water-dioxane of cyclo-octene and -hexene homolytic cleavage of the 0-0 bond plays an essential part [771, 772], and that this is so for similar oxidation of alkanes (e.g. of cyclohexane to cyclohexanol) [771],... 

RuCl(EDTA.H]702/water-dioxane/37-62°C (epoxidation of cyclo-octene)... 

Ru(C. 35C(0)CH2C(0)C. j5)3] , a substituted (acac) complex, is made from the 1,3-diketone C j COCH COC Fu with RuClj (quoted as RuCl in the paper) in ethanol with KCHCOj). In biphasic solvents [Ru(C jjC(0)CH2C(0)C j3)3]7per-fluorodecaUn-toluene/O (1 atm)/65°C oxidised aldehydes to ketones, disubstituted alkenes (cyclo-octene, norbomene) to epoxides and sulfides to sulfoxides or sul-fones [821, 822],... 

Ru PW33(0)3j(dmso)] is made from K [ PW 03, ] aqueous cis-RuCl2(dmso) under microwave irradiation IR, and Ru NMR spectra were recorded. With [Ru PW (0)3 (dmso)] 7aq. Na(10 ) cyclo-octene gave suberic acid, while with [Ru PWj 1(0)3, (dmso)] 7aq. Oxone / Bu(HSO )/DCE/50°C ada-mantane gave 1-adamantanol and 1-chloroadamantane as the main products [825]. No information was given on the nature of the effective catalyst - it is likely that some RuO at least would have been generated. 

RuCl2(dinso)2(pcbo) (pcbo=iV-phenylcarbamoyl derivative, with H, Me, OMe, Cl or NO as a p-substituent) is made from cw-RuCl Cdmso) and the ligand. As RuCl2(dmso)2(pcbo)/PhlO/water- CHjCN it epoxidised norbomene and cis-cyclo-octene [950],... 

The first Ru-catalysed epoxidation was reported in 1983 by James et al. using RuBr(PPh3)(OEP)/PhlO/CH2Cl2 with styrene, norbomene and aT-stilbene in low yields cf. mech. Ch. 1 [23]. Eater work showed that fran -Ru(0)2(TMP)/02/CgHg catalysed aerobic alkene epoxidation of cyclo-octene, cis- and trans- -methylstyrenes and norbomene (Fig. 1.26) [24],... 

Much exploratory work has been done on model substrates. Epoxidations of cyclo-octene and styrene give relatively clean products, and several studies have also been carried out on styrene, norbomene and 1-octene. 

For cyclo-octene and -hexene, styrene, stilbenes, norbomene and 1-octene, cf. 3.1.1.1 ... 

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