7094-26-0Relevant academic research and scientific papers
Alkylation of alkenes: Ethylaluminum sesquichloride-mediated hydro-alkyl additions with alkyl chloroformates and di-tert-butylpyrocarbonate
Biermann, Ursula,Metzger, Juergen O.
, p. 10319 - 10330 (2007/10/03)
A general method for the hydro-alkyl addition to the nonactivated C=C double bond of alkenes using alkyl chloroformates (primary, secondary), 12, and di-tert-butylpyrocarbonate, 52, mediated by ethylaluminum sesquichloride (Et3Al2Cl3) has been developed. Reaction of 12 and 52, respectively, with Et3Al2Cl3 gives an alkyl cation which is added to the alkene; hydride transfer to the adduct carbenium ion or, if applicable, 1,2-H shift followed by hydride transfer from Et3Al2Cl3 to the rearranged adduct carbenium ion gives the saturated addition product. The reaction has been applied to 1-alkenes, 2-methyl-1-alkenes, internal double bonds, and to three cyclic alkenes. Special interest has been focused on alkylations of unsaturated fatty compounds, such as oleic acid (2), which are important renewable feedstocks. 2-Methylalkanes, 3-methylalkanes, 2,4-dimethylalkanes, 2,3-dimethylalkanes, 2,2,4-trimethylalkanes, cyclohexylalkanes, and carboxylic acids and esters with the respective branched alkyl chain have been synthesized with good to moderate yields.
Oxidative transformations of cyclohexane, methylcyclopentane, and pentane on treatment with superelectrophiles based on polyhalomethane and aluminum halides
Akhrem,Churilova,Vitt
, p. 81 - 87 (2007/10/03)
Cyclohexane and methylcyclopentane dimerize into dimethyldecalins on treatment with superelectrophilic systems containing polyhalomethanes (CBr4, CCl4, CHCl3) and aluminum halides (AlBr3, AlCl3). At 2
Dehydration Studies of α- and β-Ionol. I With Hexamethylphosphoric Triamide
Whitfield, Frank B.,Sugowdz, Galina
, p. 591 - 600 (2007/10/02)
α-Ionol (2) when heated under reflux with hexamethylphosphoric triamide gave principally one product (1'E)-6-(buta-1',3'-dienyl)-1,5,5-trimethylcyclohex-1-ene (4a) together with trace quantities of the (1'Z)-isomer (4b).Under similar conditions β-Ionol (3) gave as major products (6E,2'E)- and (6Z,2'E)-6-(but-2'-enylidene)-1,5,5-trimethylcyclohex-1-ene (1a) and (1b) together with smaller quantities of (1'E)-1-(buta-1',3'-dienyl)-6,6-dimethyl-2-mehtylenecyclohexane (8) and 1,1,6-trimethyl-1,2,3,4,5,6-hexahydronaphtalene (9).Minor products from this reaction includedthe isomeric trienes (1c) and (1d).Reaction pathways are suggested for the formation of all identified products.
