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For lithium-free Wittig reactions, studies support a concerted formation of the oxaphosphetane without intervention of a betaine. In particular, phosphonium ylides 1 react with carbonyl compounds 2 via a [2+2] cycloaddition that is sometimes described as having [π 2 s + π 2 a] topology to directly form the oxaphosphetanes 4a and 4b.
Wittig reagents are usually described as a combination of two resonance structures: Ph 3 P + CR 2 − ↔ Ph 3 P=CR 2. The former is called the ylide form and the latter is called the phosphorane form, which is the more familiar representation. Crystallographic characterization of methylenetriphenylphosphorane shows that the phosphorus atom is ...
Tandem Wittig–Claisen reaction has also been applied to the construction of the spiro[pyrrolidin-3,3’-oxindole] ring system in natural products such as horsfiline. [2] The synthesis started with a simple o-nitrobenzaldehyde. A Wittig–Claisen reaction sequence converted the starting material to a 4-pentenal derivative that could serve as a ...
The [2,3]-Wittig rearrangement is the transformation of an allylic ether into a homoallylic alcohol via a concerted, pericyclic process. Because the reaction is concerted, it exhibits a high degree of stereocontrol, and can be employed early in a synthetic route to establish stereochemistry.
A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. [1] The reaction is named for Nobel Prize winning chemist Georg Wittig. [2] [3] The intermediate is an alkoxy lithium salt, and the final product an alcohol.
The estimated pK a of this carbon acid is near 15. [2] Potassium tert-butoxide has been used in place of butyl lithium. [3] Sodium amide has also been used a base. [4] Methylenetriphenylphosphorane is used to replace oxygen centres in aldehydes and ketones with a methylene group, i.e., a methylenation: R 2 CO + Ph 3 PCH 2 → R 2 C=CH 2 + Ph 3 PO