Publication

a-Substitution plus carbonyl olefination via b-oxido phosphorus ylids (S.C.O.O.P.Y.-reactions) scope and stereoselectivity

Manfred Schlosser
1971
Journal Articles

Abstract

Consecutive treatment of HOCH2CH2P+Ph3 Br- with BuLi, BzH, BuLi, and H2O afforded trans-PhCH:CHCH2OH in 95% isomeric purity and PhCH(OH)CH:CH2. The stereospecificity of the S.C.O.O.P.Y.-reactions (Schlosser, M. and Christmann, F. K., 1969) is discussed. [on SciFinder (R)]

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Manfred Schlosser
1971
Journal Articles

Abstract

Official source

Related concepts (9)

Peterson olefination

The Peterson olefination (also called the Peterson reaction) is the chemical reaction of α-silyl carbanions (1 in diagram below) with ketones (or aldehydes) to form a β-hydroxysilane (2) which eliminates to form alkenes (3). Several reviews have been published. One attractive feature of the Peterson olefination is that it can be used to prepare either cis- or trans-alkenes from the same β-hydroxysilane. Treatment of the β-hydroxysilane with acid will yield one alkene, while treatment of the same β-hydroxysilane with base will yield the alkene of opposite stereochemistry.

Wittig reaction

The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most often, the Wittig reaction is used to introduce a methylene group using methylenetriphenylphosphorane (Ph3P=CH2). Using this reagent, even a sterically hindered ketone such as camphor can be converted to its methylene derivative.

Substitution reaction

A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic.

Related publications (2)

a-Substitution plus carbonyl olefination via b-oxido phosphorus ylids (S.C.O.O.P.Y.-reactions) scope and stereoselectivity

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EXPRESS: How are grouping and interference related in crowding?

Metallierung und Abwandlung funktionell substituierter Alkene