The strong non-ionic base P(MeNCH 2 -CH 2 ) 3 N 1 is an efficient base for conversion of [RCH 2 PPh 3 ]X and RCH 2 P(O)(OEt) 2 to their corresponding ylides under mild conditions. Reaction of the ylides (generated in situ) with benzaldehyde give the corresponding alkenes in high yield.
ChemInform Abstract: P(MeNCH2CH2)3N: An Efficient Nonionic Superbase for Wittig and Wittig—Horner Reactions.
✍ Scribed by Zhigang Wang; John G. Verkade
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 33 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
P(MeNCH 2 CH 2 ) 3 N: An Efficient Nonionic Superbase for Wittig and Wittig-Horner Reactions.
-The strong non-ionic title base effectively deprotonates triphenylphosphonium salts (I) and phosphonates (IV) under mild conditions. Reaction of the ylides generated with aldehydes provides an efficient access to corresponding alkenes in high yields. In accordance with classical Wittig reactions, the stereochemistry of these reactions depends on the stability of the ylides.
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