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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.
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 ...
Wittig reaction; Wittig rearrangement: 1,2-Wittig rearrangement; 2,3-Wittig rearrangement; Wittig–Horner reaction; Wohl degradation; Wohl–Aue reaction; Wohler synthesis; Wohl–Ziegler reaction; Wolffenstein–Böters reaction; Wolff rearrangement; Wolff–Kishner reduction; Woodward cis-hydroxylation; Woodward–Hoffmann rule; Wulff ...
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 ...
I really like your Schlosser modification image. Don't knock your own images. I think they are great. ~K 04:05, 2 Jun 2005 (UTC) As you see below, the fact that phenyl groups are almost always used may have clouded our picture of the reaction. I think the fact is the reaction is poorly understood. Eugene Kwan 18:46, 17 December 2005 (UTC)
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.
An example of the aza-Wittig-reaction being utilized in organic synthesis is the synthesis of (–)-benzomalvin A. Two intramolecular aza-Wittig-reactions were used to construct the seven-membered ring and the six-membered ring in the molecule's skeleton. [1] Synthesis of (−)-Benzomalvin A via multiple aza-Wittig-reactions
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