Synthesis of alkyl-branched fatty acids

A general method forcyclohexylalkanes the hydro-alkyl addition to the non-activated carbon-carbon double bond of alkenes with alkyl chloroformates (primary, secondary), 12, and di-tert-butylpyrocarbonate, 52, was mediated by ethyl aluminum (Et3Al2Cl3) was developed. The reaction of 12 and 52 each are an alkyl cation with Et3Al2Cl3 that is added to the alkene, hydride transfer to the adduct carbenium ion, or possibly, 1,2-H shift by hydride transfer from the newly Et3Al2Cl3 Adduktcarbeniumion followed is the saturated adduct ions. The reaction was applied to 1-alkenes, 2-methyl-1-alkenes, internal double bonds, and three cyclic alkenes. Particularly interested in alkylations of unsaturated fats such as oleic acid (2), the major renewable resources are concentrated. , 2-methyl alkanes 3-methyl alkanes, 2,4-dimethylalkanes, 2,3-dimethylalkanes, 2,2,4-trimethylalkanes, cyclohexylalkanes and carboxylic acids and esters, synthesized wherein the respective branched alkyl chain with good to moderate yields. Mixed anhydrides of N-tert-butoxycarbonyl, N-​​benzyloxycarbonyl-and N-9-fluorenylmethoxycarbonyl amino acids were using isopropyl chloroformate, and by edulcoration. They were more stable than the corresponding anhydrides using ethyl and isobutyl chloroformates. Aminolysis of the anhydrides of an amino acid ester were successful, the amount of the urethane reaction at the carbonate group wherein the same as the other of cyclohexylalkanes the anhydrides is generated. Racemization participate in the coupling of N-benzyloxycarbonylglycylamino acids was by the mixed anhydride method with isopropyl chloroformate a third to a quarter of the observed that for the same couplings with ethyl and isobutyl chloroformate.

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