14633-95-5

Usage

Uses

Used in Organic Synthesis:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as a reagent for the Wittig reaction, a method for the formation of carbon-carbon double bonds. It is utilized for the creation of complex organic molecules.
Used in Pharmaceutical Industry:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as an important intermediate in the pharmaceutical field, aiding in the synthesis of various pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical industry, CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is used as a key intermediate for the synthesis of agrochemical products.
Used in Materials Science:
CYCLOPROPYLIDENETRIPHENYLPHOSPHORANE is also used in materials science, contributing to the development of new materials through its role in organic synthesis.

Upstream product

• 76757-83-0 Cyclopropyltriphenylphosphonium-tetrafluoroborat 
• 603-35-0 triphenylphosphine 
• 109-64-8 1,3-dibromo-propane 
• 873332-53-7 6-(4-nitro-phenyl)-4,4,4-triphenyl-5-oxa-4λ⁵-phospha-spiro[2.3]hexane-6-carboxylic acid methyl ester 
• 14114-05-7 cyclopropyltriphenylphosphonium bromide 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 

Downstream Products

• 20355-86-6 4,4,4,6-tetraphenyl-5-oxa-4λ⁵-phospha-spiro[2.4]heptane 
• 20355-89-9 4,4,4,7-tetraphenyl-5-oxa-6-aza-4λ⁵-phospha-spiro[2.4]hept-6-ene 
• 79012-40-1 (cyclopropylidene-2 ethyl)-2 methyl-2 dioxolanne-1,3 
• 7632-57-7 diphenylmethylenecyclopropene 
• 58992-26-0 1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat 
• 41418-59-1 1-methyl-1-phenylmethylenecyclopropane 
• 163011-27-6 1-(2-t-butyldimethylsiloxy-4-methylphenyl)-1-cyclopropylideneethane 
• 155397-51-6 (2-Cyclopropylidene-propylsulfanyl)-benzene 
• 98885-74-6 (3-Methoxypropyl)triphenylphosphonium-hexafluorophosphat 
• 98885-68-8 Methyldiphenyl<1-(triphenylphosphonio)cyclopropyl>phosphonium-bis(hexafluorophosphat) 
• 98906-24-2 C₃₅H₃₆OP₂⁽²⁺⁾*2F₆P^(1-) 
• 214116-83-3 di(4-chlorophenyl)methylenecyclopropane 
• 147356-80-7 p-phenylcyclohexylidenecyclopropane 
• 55088-80-7 1-(cyclopropylidenemethyl)-4-methylbenzene 

Relevant academic research and scientific papers

Activation and Functionalization of C-C σ Bonds of Alkylidene Cyclopropanes at Main Group Centers

Aluminum(I) and magnesium(I) compounds are reported for the C-C σ-bond activation of strained alkylidene cyclopropanes. These reactions result in the formal addition of the C-C σ bond to the main group center either at a single site (Al) or across a metal-metal bond (Mg-Mg). Mechanistic studies suggest that rather than occurring by a concerted oxidative addition, these reactions involve stepwise processes in which substrate binding to the main group metal acts as a precursor to α- or β-alkyl migration steps that break the C-C σ bond. This mechanistic understanding is used to develop the magnesium-catalyzed hydrosilylation of the C-C σ bonds of alkylidene cyclopropanes.

Ring opening of methylenecyclopropanes with halides in liquid sulfur dioxide

Methylenecyclopropanes (MCP) undergo ring opening reactions with group I and II metal halides and ammonium halides in liquid SO2 to afford homoallylic halides, which are versatile reagents in organic synthesis. The developed reaction conditions are compatible with acid-labile substrates such as N-Boc-protected compounds. Liquid SO2 is a polar reaction medium with Lewis acid properties that solubilizes inorganic salts. The unique properties of SO2 were demonstrated by control experiments: 1) upon performing the reactions with the aforementioned salts in conventional solvents, the MCP ring opening was not observed either in the presence of catalytic amounts of H3PO4 (similar pKa to that of H2SO3), or in the absence of H3PO4; 2) a solution of SO2 in THF exhibited similar properties to that of liquid SO2.

Organoselenium-Catalyzed Oxidative Ring Expansion of Methylenecyclopropanes with Hydrogen Peroxide

Catalyst screening and optimization of reaction conditions allowed control of the organoselenium-catalyzed oxidative ring expansion of highly active methylenecyclopropanes to give substituted cyclobutanones selectively. This protocol employs H2O2 as a clean oxidant and generates no waste and, therefore, provides green access to useful, but not readily available, substituted cyclobutanones under mild conditions.

Combined rhodium-catalyzed carbon-hydrogen activation and β-carbon elimination to access eight-membered rings

(Figure Presented) Enlargel C-H bond activation and β-carbon elimination are combined in a net intramolecular hydroacylation of alkylidenecyclobutanes and alkylideneazetidines in the presence of rhodium catalysts, affording eight-membered-ring compounds in high yield (see scheme). This study demonstrates the possibility of exploiting the strain energy of azetidines through β-carbon elimination in new transition-metal-catalyzed reactions.

First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane

1,2-Oxaphosphetanes bearing three phenyl groups directly bound to the phosphorus atom were successfully isolated for the first time as stable crystals in the typical Wittig reaction of cyclopropylidenetriphenylphosphorane with activated carbonyl compounds. X-ray analysis of the oxaphosphetane showed that the phosphorus atom is at the center of a slightly distorted trigonal bipyramidal structure. Thermal decomposition of these oxaphosphetanes was carried out to give the starting carbonyl compounds and Wittig reaction products, olefins.

NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl) cyclobutanols with aryl iodides. Stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones

Equation presented. A novel type of cascade ring expansion process has been developed by the palladium-catalyzed reaction of (Z)-1-(1,3-butadienyl) cyclobutanols with aryl iodides. The reaction proceeds in a stereospecific manner to produce (Z)-2-(3-aryl-

Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol

Mixtures of (E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from α,α-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through π-1,1- trimethyleneallylpalladium complexes formed upon treatment with palladium(0), a new and convenient entry to the diastereomeric four-membered ring monoterpenoids (±)-fragranol and (±)-grandisol.

Asymmetric dihydroxylations of aromatic cyclopropylidenes

A number of aromatic cyclopropylidenes have been converted to diols using the Sharpless asymmetric dihydroxylation (AD) procedure. The enantiomeric ratios were determined by chiral phase HPLC by comparison with their racemates.

Synthetic potentialities of alkyl and aryl cyclopropylidenealkyl sulfides: Access to 1-(arylthio)vinylcyclopropanes by a 1,3-shift of an arylthio group

Alkyl and aryl cyclopropylidenealkyl sulfides 2, 4 and 5 were converted to give access to 1-(arylthio)vinylcyclopropanes 3 by light induced or acid catalyzed 1,3-shift of the arylthio group. Some results on the reactivity of sulfides 2, 4 and 5 are report