Industrial applications of the wittig reaction

Pommer, Horst; Thieme, P.

doi:10.1007/bfb0018058

Cited by 69 publications

(21 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Terpenes are secondary metabolites widespread in nature (plants, marine organisms as well as fungi) and presenting interesting applications in industry. [17a] The awakening for Wittig reaction use in terpene synthesis was done by industrial investigations and due to their interest in the synthesis of vitamin A and later on extended to other carotenoids . Around this time was developed the first Wittig reaction variation, consisting mainly in the use of dialkylphosphonate as an anion‐stabilizing group to replace the triphenylphosphonium salt moiety, and the industrial synthesis of β‐carotene.…”

Section: Total Synthesis Of Natural Heterocyclic Compoundsmentioning

confidence: 99%

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

View full text Add to dashboard Cite

More than sixty years after its discovery, the Wittig reaction still is a powerful tool to create carbon–carbon double bonds. The large diversity of high‐yielding and stereoselective reactions that can be achieved, even for highly functionalized molecules, is presented, demonstrating that the Wittig reaction is an efficient and attractive strategy in synthetic organic chemistry. The principles of the reaction will be briefly presented and discussed, but the focus will be on the most recent reports using this reaction in the synthesis of heterocyclic compounds. A comprehensive discussion on its application in the total synthesis of natural products and in the synthesis of natural analogues will be presented. Emphasis will be given to important organic molecules that present interesting biological activities. The purpose of this short review is to highlight the advances in this general area by presenting such newer applications in organic synthesis and eventually guide future researchers.

show abstract

Section: Total Synthesis Of Natural Heterocyclic Compoundsmentioning

confidence: 99%

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

View full text Add to dashboard Cite

show abstract

“…The main method that became the basis for industrial manufacture was that involving the Wittig reaction (originally discovered by Georg Wittig in 1954), which later resulted in another Nobel Prize for chemistry. A three‐stage procedure adopted by BASF (Germany) starting with β‐ionone, produced vinyl‐β‐ionol, the phosphonium chloride of which was then condensed with two molecules of a symmetrical C 10 dialdehyde [67]. The same Wittig reaction can be also used for the production of both β‐apo‐8′‐carotenal (E160e) and the ethyl ester of the corresponding carotenoid acid (E160f), but in this synthesis only a 1:1 molecular proportion of the two reactants is used.…”

Section: Biosynthesis Vs Laboratory Synthesismentioning

confidence: 99%

Biosynthesis and synthesis of natural colours

Dawson¹

2009

Coloration Technology

View full text Add to dashboard Cite

In nature, the detection of colours requires an organism having some type of eye with a retina and two or three types of photoreceptor connected to a nervous system, which can interpret the signals received. Evidence that certain simple organisms were coloured 1 billion years ago, and some more advanced creatures, which could have possessed eyes a few hundreds of million years ago, is exemplified. A vast array of chemicals essential to life are produced by living organisms and their biosynthesis depends upon individual genetic patterns, which determine the enzyme catalysts involved. Plants photosynthesise many pigments, which are essential for them to maximise the absorption of energy from the sun, while others offer protection from any harmful radiation. Such pigments, for example chlorophylls and the carotenoids, flavonoids and betalains, have traditionally been used as natural dyes, food colorants and medicines. This review compares the chemical processes involved in their biosynthesis and the laboratory methods adopted to confirm their chemical structure. Some engineered biosynthetic methods are now used for commercial production of natural colours and these methods may involve the controversial use of genetic engineering.

show abstract

“…According to [21], [56], if the base does not contain lithium, the ylide is said to be prepared under salt-free conditions. It became apparent that most triphenylphosphonium salts with a negative charge on the a-carbon atom react even with weaker bases than phenyllithium, yielding the corresponding ylides, usually in good yields [57], [58]. Suitable proton acceptors include alkali metal alkoxides and sodium amide [57], [59].…”

Section: Usesmentioning

confidence: 99%

“…When sodium ethoxide or methoxide is used as a proton acceptor [53], [58] with the corresponding alcohol as solvent, the alcoholate anion removes a proton from the phosphonium salt. The methylenetriphenylphosphorane is formed in solution according to the equation:…”

Section: Usesmentioning

confidence: 99%

Sodium Amide

Lange¹,

Triebel²

2000

Ullmann's Encyclopedia of Industrial Chemistry

View full text Add to dashboard Cite

The article contains sections titled: 1. Introduction 2. Properties 2.1. Physical Properties of a Solution of Sodium in Liquid Ammonia 2.2. Physical Properties of Sodium Amide 2.3. Chemical Properties 2.3.1. Chemical Properties of Na ‐ NH 3 Solution 2.3.2. Chemical Properties of Sodium Amide 3. Production 4. Safety Aspects 5. Uses 6. Transport Regulations

show abstract

Industrial applications of the wittig reaction

Cited by 69 publications

References 50 publications

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Biosynthesis and synthesis of natural colours

Sodium Amide

Contact Info

Product

Resources

About