Synthesis alcohols from ethylene derivs

Trialkylboranelhydrogen peroxide-irradiation Synthesis of alcohols from ethylene derivs. 

Boron fluoride/sodium tetrahydridoborate Alcohols from ethylene derivatives Asym. synthesis... 

The development 0/ the chemistry of boranes continues with outstanding results It has produced a convenient route to the less stable, terminally unsaturated compounds from the more stable, highly substituted ethylene derivatives , a facile procedure for the asymmetric synthesis of alcohols of high optical purity , and a... 

Clearly, the slate of chemicals produced from coal-derived synthesis gas will expand as new technologies are developed, and supplies of petroleum and natural gas dwindle. The most likely such chemicals are those for which existing processes have been demonstrated but which presently lack economic merit. Relatively small improvements in technology, shifts in feedstock availability, capital costs, or political factors could enhance the viability of coal-based processes for the production of methanol, ethanol, and higher alcohols, vinyl acetate, ethylene glycol, carboxylic acids, and light olefins. 

An efficient synthesis of ( )-quebrachamine is based on the construction of a suitable precursor via ring cleavage of an a-diketone monothioketal (810) (80JCS(P1)457). This monothioketal, available from 4-ethoxycarbonylcyclohexanone ethylene ketal, was fragmented to the dithianyl half ester (811) with sodium hydride in the presence of water. Reaction of (811) with tryptamine and DCC provided an amide which was converted to the stereoisomeric lactams (812) on hydrolysis of the dithiane function. Reduction of either the a- or /3-ethyl isomer with lithium aluminum hydride followed by conversion of the derived amino alcohol to its mesylate produced the amorphous quaternary salt (813). On reduction with sodium in liquid ammonia, the isomeric salts provided ( )-quebrachamine (814 Scheme 190). 

Fundamental work on organoaluminum chemistry by Prof. Karl Ziegler and co-workers at the Max Planck Institute provided the basis for a commercial synthesis of even-carbon-numbered straight chain primary alcohols. These alcohols are identical with products derived from naturally occurring fats. In this process, ethylene is reacted with aluminum triethyl to form a higher aikylaluminum which then is oxidized and hydrolyzed to give the corresponding alcohols. 

Ethylene (Ethene) (bicarburetted hydrogen, ethene) n. A colorless, flammable gas derived by cracking petroleum and by distillation from natural gas. In addition to serving as the monomer for polyethylene, it has many uses in the plastics industry including the synthesis of ethylene oxide, ethyl alcohol, ethylene glycol (used in making alkyd and polyester resins), ethyl chloride, and other ethyl esters. Properties molecular weight, 28 bp, — 1.025°C Sp gr of liquid, 0.610/0°C. 

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