Publication

SCOOPY-Reaktionen : Die Regioselektivität der Alkenol-Synthese

Manfred Schlosser
1972
Journal Articles

Abstract

Ph3P+CH2R (R = H, Me) reacted with aldehydes R1CHO (R1 = n-C5H11, Me2PrC, Ph) in the presence of BuLi and HCHO to give primary alkenols R1CH:CRCH2OH; ketones R2R3CO [R2, R3 = Me, Ph or (CH2)4, (CH2)5] and spatially crowded aldehydes gave secondary and tertiary alcs. R2R3C(OH)CR:CH2. A b-oxido phosphonium ylide was a reaction intermediate. [on SciFinder (R)]

Official source

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Manfred Schlosser
1972
Journal Articles

Abstract

Official source

Related concepts (6)

Aldehyde

In organic chemistry, an aldehyde (ˈældᵻhaɪd) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen.

Acetaldehyde

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption.

Dimethyl sulfoxide

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin.