Publication

Carbonyl olefination with a-substitution

Manfred Schlosser
1969
Journal Articles

Abstract

Deprotonated phosphorus betaines react with D, alkyl, or halogen donors to form a-substituted derivs. which decomp. either spontaneously or after "activation" to give Ph3PO and olefins with the substitution occurring on one of the olefinic carbons. This represents a versatile preparative scheme for new compounds. The reaction is stereoselective, giving mainly the trans isomer except when the original phosphonium salt contains a Me group, e.g. MePh3PX. A suspension of 30 millimoles PrPh3PBr in 60 ml tetrahydrofuran was stirred under N 30 min at -20 Deg with 30 millimoles 0.9M ethereal PhLi contg. LiBr, 30 millimoles BzH added at -78 Deg, 30 millimoles PhLi added to decolorize the soln., the temp. rose to -30 Deg, 50 millimoles MeI was added, after rapid stirring the temp. rose to 0 Deg, and 45 millimoles KOCMe3 was added. Removal of the solvent gave 55% mixt. of cis- and trans-b-ethylstyren e, (cis-trans = 3:97), b. 91-3 Deg. In a similar manner the following compds. were prepd. cis- and trans-styre ne-w-d, Me2C:CHPh, trans-EtMeC:CHPh, trans-4-fluoro-3-heptene, cis-MeFC:CHPh, 4-fluoro-1-phenyl-1,3-butadiene, 3-tetrahy-dropyranyloxy-17-[3-fluoro-cis-2-pentene-2-yl]androst-5-ene, cis-MeClC:CHPh, and cis-MeBrC:CHPh. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/2b187c62-1e01-4977-900f-c36d2a96280f

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Manfred Schlosser
1969
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/2b187c62-1e01-4977-900f-c36d2a96280f

About this result

Related concepts (4)

Trans fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year.

Omega-3 fatty acid

Omega−3 fatty acids, also called Omega−3 oils, ω−3 fatty acids or n−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond, three atoms away from the terminal methyl group in their chemical structure. They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology. The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).

Ethylene oxide

Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.