15935-94-1

Usage

Uses

Used in Organic Synthesis:
Allylidenetriphenylphosphorane is utilized as a reagent in organic synthesis, specifically for the preparation of alkenes from aldehydes and ketones. It serves as a key component in the Wittig reaction, a widely employed method for the synthesis of alkenes, which are fundamental building blocks in organic chemistry.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Allylidenetriphenylphosphorane is used as a crucial intermediate in the synthesis of various medicinal compounds. Its ability to form alkenes from carbonyl compounds is essential for the creation of complex molecular structures that exhibit therapeutic properties.
Used in Perfumery and Flavor Industry:
Allylidenetriphenylphosphorane is also employed in the production of perfumes and flavors, where it contributes to the formation of specific aromatic compounds that impart distinctive scents and tastes to products.
Used in Research and Development:
In the realm of scientific research, Allylidenetriphenylphosphorane is a valuable tool for exploring new chemical reactions and developing innovative synthetic pathways. Its versatility and reactivity make it an indispensable component in the advancement of organic chemistry.
Used in Industrial Processes:
Within the chemical industry, Allylidenetriphenylphosphorane is widely used in various industrial processes to produce a range of products, from specialty chemicals to consumer goods. Its role in the synthesis of alkenes is particularly important for the manufacturing of polymers, plastics, and other materials that are integral to modern industry.

Upstream product

• 603-35-0 triphenylphosphine 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 865-47-4 potassium tert-butylate 
• 18480-23-4 allyltriphenylphosphonium chloride 
• 109-72-8 n-butyllithium 
• 591-51-5 phenyllithium 

Downstream Products

• 73505-47-2 trans,cis-1-phenyl-1,3,5-hexatriene 
• 18480-23-4 allyltriphenylphosphonium chloride 
• 54697-94-8 2-[(E)-3-(Triphenyl-λ⁵-phosphanylidene)-propenyl]-quinoline 
• 97478-23-4 2-((E)-Buta-1,3-dienyl)-3-phenyl-1-(toluene-4-sulfonyl)-aziridine 
• 95054-78-7 2-((E)-Buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-cyclopropanecarboxylic acid ethyl ester 
• 116498-65-8 (2S,3R,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al 
• 116384-34-0 (2R,3S,4R,5E)-2,3,4-tribenzyloxyocta-5,7-diene-1-al 
• 116498-64-7 (2R,3S,4R)-tribenzyloxy-octa-5(Z),7-diene-1-al diethyl dithioacetal 
• 116384-33-9 (2R,3S,4R)-tribenzyloxy-octa-5(E),7-diene-1-al diethyl dithioacetal 
• 125153-26-6 [((Z)-1-Buta-1,3-dienyl)-heptylsulfanyl]-benzene 
• 125153-25-5 [((E)-1-Buta-1,3-dienyl)-heptylsulfanyl]-benzene 
• 29837-19-2 (3E,5Z,8Z)-1,3,5,8-undecatetraene 
• 116384-36-2 (1R,2R,3S,3aR,7aS)-1,2,3-Tris-benzyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 18304-14-8 (E)-6-methyl-1,3,5-heptatriene 

Relevant academic research and scientific papers

One-pot synthesis of 1-pentafluorophenyl-1,3-dienes

Perfluorobenzene was added to allylidenetriphenylphosphorane regiospecifically, after transylidation, to give (3-pentafluorophenyl)allylidenetriphenylphosphorane, which reacted with aldehydes to afford 1-pentafluorophenyl-1,3-dienes in good to excellent y

Free radical cyclizations of trienes with tris(trimethylsisyl)silane

The intramolecular trapping of a stabilized intermediate allylic radical generated by the addition of tris(trimethylsilyl)silyl (sisyl) radical to a conjugated system was performed. The observed low stereoselectivity suggests thermodynamic rather than kinetic control in this cyclization process.

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Heavier Carbonyl Olefination: The Sila-Wittig Reaction

The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Sia? CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.

Competitive 1,2-C Atom Shifts in the Strained Carbene Spiro[3.3]hept-1-ylidene Explained by Distinct Ring-Puckered Conformers

Spiro[3.3]hept-1-ylidene is a markedly strained carbene reaction intermediate that was generated by high-vacuum flash pyrolysis (HVFP) of the corresponding p-tosylhydrazone sodium salt. Five hydrocarbons were produced from the Bamford-Stevens reactant in 82% overall yield. The carbene undergoes two [1,2]-sigmatropic rearrangements via competing 1,2-C atom shifts. Ring-contraction yields cyclopropylidenecyclobutane, while ring-expansion affords bicyclo[3.2.0]hept-1(5)-ene. The ring contraction is regiospecific despite the formation of some 1-methylenespiro[2.3]hexane. It does not originate from the carbene under HVFP conditions. Instead, it comes from a methylenecyclopropane-type rearrangement of chemically activated cyclopropylidenecyclobutane. Similarly, some chemically activated bicyclo[3.2.0]hept-1(5)-ene rearranges to 1,2-dimethylenecyclopentane via electrocyclic ring-opening. Accounting for the conversion of primary products to secondary ones, relative yields indicate that ring-contraction within the carbene prevails over ring-expansion by a factor of 6.7:1. Computational chemistry was used to assess the structures, conformations, energies, strain energies, transition states, and activation energies of these rearrangements with the goal of explaining product selectivities. The dual-ringed carbene is predicted to assume four distinct geometric conformations that have a bearing on transition-state selection. The reactive cyclobutylidene units of two conformers are significantly puckered, like cyclobutylidene itself, while those of the other two are flatter. The selectivity of the title carbene is compared with that of spiro[2.3]hex-4-ylidene.

Novel One-pot Synthesis of 1-Iodo-1-trimethylsilyl 1,3-Dienes

Iodine was added to 3-(trimethylsilyl)allylic phosphonium ylide regiospecifically to give 3-iodo-3-trimethylsilyl allylic phosphonium ylide, which reacted with carbonyl compounds to give 1-iodo-1-trimethylsilyl 1,3-dienes with high stereoselectivity in good yield.

Energetics of P, S, and N Ylide Formation and Reaction in Solution

Calorimetric heats of deprotonation for several carbon acid precursors of P, S, and N ylides are reported in DMSO at 25 deg C.The ylide obtained from benzyltrimethylammonium bromide undergoes the Sommelet-Hauser rearrangement immediately after its formati

A novel synthesis of trans-γ,δ-unsaturated trifluoromethyl ketones

A novel γ-trifluoroacetylation and a novel ylide-anion formation via conjugated nucleophilic addition and their application to the synthesis of trans-γ,δ-unsaturated trifluoromethyl ketones are described.

A new one-pot synthesis of silylated 1,3-dienes

A new convenient one-pot synthesis of substituted silylated 1,3-dienes starting from the commercial available substances is described.

Reaction of Diphenylcyclopropenone with Allylidenetriphenylphosphoranes

Allylidenetriphenylphosphoranes 2 react with diphenylcyclopropenone (1) via a ring opening mechanism.While reaction of 2a and 2b yields the bicyclic phosphane 3 through the zwitterion 4 as intermediate, two equivalents of 2c react with 1 to produce the al