2- 2- alkane epoxide

The occurrence of hydrocarbons (usually mono- and di-alkenes) with an epoxide function group have been reported usually as sex attractants. The sex attractant of the female gypsy moth, Lymantria dispar, was identified as the C18 2-methyl alkane derivative cis-7,S-epoxy-2-methyloctadecane (Bierl et al 1972). For the housefly, M. domestica, a major sex pheromone component is the C23 -alkane epoxide d.v-9,1O-cpoxytricosane (Uebel et al 1978) with a lesser quantity of 9,10-epoxyheptacosane (Mpuru et al., 2001). 

Li[Et3BH] (Superhydride) (lithium triethylborohydride) Tetrahydrofuran -78 to RT ester —> alcohol ketone —> alcohol aldehyde —> alcohol alkyl halide —> alkane epoxide —> alcohol... 

Na[AlH2(OCH2CH20CH3)2l (RED-AL) (sodium bis-[2-methoxyethoxy]-aluminium hydride) Ethers, toluene -78 to RT ester — alcohol ketone — alcohol aldehyde — alcohol alkyl halide — alkane epoxide — alcohol Dt,U-unsaturated enone —> allvlic alcohol... 

Lignin can be grafted with alkane epoxides to form polyether adducts and this reaction has been extensively studied by the research group of Dr. Wolfgang Glasser at Virginia State University and Polytechnic Institute. The reaction is initiated by base attack on... 

Substitutive lUPAC nomenclature names epoxides as epoxy derivatives of alkanes According to this system ethylene oxide becomes epoxyethane and propylene oxide becomes 1 2 epoxypropane The prefix epoxy always immediately precedes the alkane ending it is not listed m alphabetical order like other substituents... 

Recall from Section 6 18 that epoxides may be named as epoxy derivatives of alkanes in substitutive lUPAC nomenclature... 

Section 16 2 The oxygen atom m an ether or epoxide affects the shape of the mole cule in much the same way as an sp hybridized carbon of an alkane or cycloalkane... 

In general, peroxomonosulfates have fewer uses in organic chemistry than peroxodisulfates. However, the triple salt is used for oxidizing ketones (qv) to dioxiranes (7) (71,72), which in turn are useful oxidants in organic chemistry. Acetone in water is oxidized by triple salt to dimethyldioxirane, which in turn oxidizes alkenes to epoxides, polycycHc aromatic hydrocarbons to oxides and diones, amines to nitro compounds, sulfides to sulfoxides, phosphines to phosphine oxides, and alkanes to alcohols or carbonyl compounds. 

Reaction conditions depend on the reactants and usually involve acid or base catalysis. Examples of X include sulfate, acid sulfate, alkane- or arenesulfonate, chloride, bromide, hydroxyl, alkoxide, perchlorate, etc. RX can also be an alkyl orthoformate or alkyl carboxylate. The reaction of cycHc alkylating agents, eg, epoxides and a2iridines, with sodium or potassium salts of alkyl hydroperoxides also promotes formation of dialkyl peroxides (44,66). Olefinic alkylating agents include acycHc and cycHc olefinic hydrocarbons, vinyl and isopropenyl ethers, enamines, A[-vinylamides, vinyl sulfonates, divinyl sulfone, and a, P-unsaturated compounds, eg, methyl acrylate, mesityl oxide, acrylamide, and acrylonitrile (44,66). 

Ca.ta.lysts, A small amount of quinoline promotes the formation of rigid foams (qv) from diols and unsaturated dicarboxyhc acids (100). Acrolein and methacrolein 1,4-addition polymerisation is catalysed by lithium complexes of quinoline (101). Organic bases, including quinoline, promote the dehydrogenation of unbranched alkanes to unbranched alkenes using platinum on sodium mordenite (102). The peracetic acid epoxidation of a wide range of alkenes is catalysed by 8-hydroxyquinoline (103). Hydroformylation catalysts have been improved using 2-quinolone [59-31-4] (104) (see Catalysis). 

The acetal polymers are probably never supplied for use without any additives being incorporated. As mentioned in Section 19.3.1 antioxidants of the phenol alkane type are present in both homopolymers and copolymers. Acid acceptors are also believed to be widely used to absorb traces of acidic materials which attack the acetal linkage. Epoxides, nitrogen compounds and basic salts have been successfully employed. 

Polyfluoroalkyl- andperfluoroalkyl-substituted CO and CN multiple bonds as dipolarophiles. Dmzo alkanes are well known to react with carbonyl compounds, usually under very mild conditions, to give oxiranes and ketones The reaction has been interpreted as a nucleophilic attack of the diazo alkane on the carbonyl group to yield diazonium betaines or 1,2,3 oxadiazol 2 ines as reaction intermediates, which generally are too unstable to be isolated Aromatic diazo compounds react readily with partially fluorinated and perfluorinated ketones to give l,3,4-oxadiazol-3-ines m high yield At 25 °C and above, the aryloxa-diazolines lose nitrogen to give epoxides [111]... 

Epoxides are normally nmned as epoxy derivatives of alkanes or as substituted oxiranes. 

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