A Useful Synthesis of Alkylidenesuccinic Acids by Wittig Reaction in Aqueous Media

Nishiyama, T.; Miyazawa, Mitsuo

doi:10.5650/jos.55.151

J. Oleo Sci.

2006

DOI: 10.5650/jos.55.151

|View full text |Cite

A Useful Synthesis of Alkylidenesuccinic Acids by Wittig Reaction in Aqueous Media

T. Nishiyama

Mitsuo Miyazawa

Abstract: 2-Carboxy-1-ethoxycarbonylethylidenetriphenylphosphorane 2 reacted with aldehydes in aqueous media under the neutral condition to afford stereoselectively the half ester of alkylidensuccinic acid in good yield as a single compound from 1 H-NMR without column chromatography in comparison with Wittg reaction in conventional organic solvent.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2010

Publication Types

Select...

Other1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Wittig Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

The synthesis of an olefin from the reaction between a carbonyl compound (aldehyde or ketone) and a phosphonium ylide, via either a betaine and/or oxaphosphetane intermediate is generally known as the Wittig reaction. Occasionally, it is also referred to as the Wittig alkenylation or Wittig process. The extension of this reaction by the application of a phosphine oxide carbanion, instead of a phosphonium ylide is known as the Horner reaction or Wittig Horner reaction, while the preparation of olefin from a phosphonate carbanion is commonly referred to as the Horner–Wadsworth–Emmons olefination. Several other extensions of this reaction have been addressed. All the reaction steps of the Wittig reaction have been discussed. The reversible process to give the carbonyl compound and phosphorane is also possible, and such reversible reaction is known as the retro ‐Wittig reaction. The most important feature of the Wittig reaction is probably the easy control of stereochemistry of olefins (i.e., either Z ‐ or E ‐configuration). It has been observed that ultimate configuration of olefins depends on many factors, such as the structure of phosphoranes, the base and the solvent used, the concentration of ylide, and the reaction temperature. In particular, the Z ‐selectivity from nonstabilized ylides can be further enhanced by replacement of the phenyl group in triphenylphosphane moiety with either a 2‐pyridyl or 2‐furyl group. It has been reported that even the replacement of one phenyl ring by a pyridyl group can apparently increase the Z ‐selectivity without affecting the yields of olefins. It has been reported that E ‐olefin is the major product in the protic solvent, whereas Z ‐olefin predominates in the Wittig reactions when carried out in aprotic media. Other facets of the Wittig reaction have also been discussed, which include, application of the catalysts and the enhancement of reactivity in organic solvent by the application of a phase‐transfer catalyst or promotion of the reaction by photochemical or microwave irradiation. This reaction has very wide applications in organic synthesis, such as transformation of unprotected carbohydrates and preparation of artificial carbon‐linked (1,6)‐oligosaccharides.

show abstract

Wittig Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

A Useful Synthesis of Alkylidenesuccinic Acids by Wittig Reaction in Aqueous Media

Cited by 1 publication

References 16 publications

Wittig Reaction

Wittig Reaction

Contact Info

Product

Resources

About