75581-74-7

Upstream product

• 57508-95-9 N-phenyl-4-methyl-3,6-endooxycarbonyl-1,2,3,6-tetrahydrophthalimide 
• 96326-62-4 endo-3-ethoxy-6-methyl-N-phenyl-2,3-oxaphosphabicyclo<2.2.2>oct-5-ene-8,9-dicarboximide 3-oxide 
• 122093-00-9 endo-3-ethoxy-6-methyl-N-phenyl-2,3-oxaphosphabicyclo<2.2.2>oct-5-ene-8,9-dicarboximide 3-sulfide 
• 122093-00-9 (1S,2R,6R,7S)-9-Ethoxy-11-methyl-4-phenyl-9-thioxo-8-oxa-4-aza-9λ⁵-phospha-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5-dione 
• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 941-69-5 N-phenyl-maleimide 
• 96326-62-4 endo-3-ethoxy-6-methyl-N-phenyl-2,3-oxaphosphabicyclo<2.2.2>oct-5-ene-8,9-dicarboxamide 3-oxide 
• 100-46-9 benzylamine 
• 132434-65-2 endo-3-(N,N-diethylamino)-6-methyl-N-phenyl-2,3-oxaphosphabicyclo<2.2.2>oct-5-ene-8,9-dicarboximide 3-oxide 

Downstream Products

• 57508-96-0 C₂₅H₂₀N₂O₄ 

Relevant academic research and scientific papers

Mechanistic Studies on Metaphosphate Generation from Fragmentation of 2,3-Oxaphosphabicyclooctene Derivatives

The rates of fragmentation of 3-R-6-methyl-N-phenyl-2,3-oxaphosphabicyclooct-5-ene-8,9-dicarboximide- 3-oxide, where R = EtN or EtO, and of the 3-sulfide, where R - EtO, were determined in various solvents and at various temperatures.All reactions were first-order, as they were also when alcohols were present as trapping agents for the released metaphosphoric acid derivatives.From the small solvent effects on rates and activation parameteers, it was concluded that the thermal fragmentations occurred by a retrocycloaddition process.This was supported by the similarity in rates for the three substrates, which differ considerably in polarity at phosphorus.The metaphosphates showed selectivity in their reactivity to alcohol mixtures; rates were faster with more nucleophilic alcohols (ethanol vs 2,2,2-trifluoroethanol) and less crowded alcohols (ethanol vs tert-butyl alcohol).A secondary reaction of the released metaphosphate with two of the substrates was detected by kinetics measurements; first-order rate constants were larger when alcohol was not present to remove metaphosphate.Quantum yields in photochemical fragmentations of the substrates were unchanged when alcohols were present; metaphosphates generated in this fashion showed selectivity effects toward alcohols as seen in the thermal fragmentation.No evidence was found for radical intermediates in either process.

Maleimide cycloadditions by sulfinyldienes: Is the sulfur configuration the only controller of the diastereofacial selectivity?

Cyclohexylsulfinyl-3-methyl-1,3-butadienes 5, 6, and 1-[1- (cyclohexylsulfinyl)ethenyl]cyclohexene (7), easily prepared from cyclohexanethiol (1) via transient cyclohexanesulfenic acid (4), were reacted with N-phenylmaleimide under different conditions, at normal and high pressure. The stereochemical outcome of these cycloadditions contributes a better understanding of the relationships among different factors controlling facial diastereoselection.

Study on the UV light-mediated fragmentation of 7-(2,4,6-trialkylphenyl-)7-phosphanorbornene 7-oxides in alcohols: new evidences on the mechanism

Preparative-scale photolyses of the title triisopropylphenyl-substituted compounds 1 and 4 at 254 nm, in the presence of alcohols, led to aryl-H-phosphinates 3 in good yields. Reaction of the tri-tertbutylphenyl derivative 5 was, however, accompanied by side reactions. The results of two series of competitive reactions are consistent with a mechanism involving a five-coordinate adduct 8 of the alcohol on the P = O group of the phosphanorbornene oxides.

Experiments on the Generation of 2-Coordinate Phosphoryl Species by Fragmentation of 7-Phosphanorbornene and 3-Phospholene Derivatives

2,6-Di-tert-butyl-4-methylphenyl phosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300 deg C (0.01 mm).Attempts to prepare 1-adamantyl phosphenite simila

The mechanism of fragmentation of alky α-(oxyimino)benzylphosphonates; use of silica gel as a novel hydroxylic trapping reactant for an intermediate alkyl metaphosphate

Silica gel was employed to react with the suspected metaphosphate intermediate of the acid-promoted cleavage of monoalkyl α-(oxyimino)benzylphosphonates. The silica gels displayed CP-MAS 31P NMR signals at about δ-8. A similar value was obtained for silica gel phosphorylated with ethyl metaphosphate from a different source (thermolysis of a P-ethoxy 2,3-oxaphosphabicyclo[2.2.2]octene derivative.

GENERATION OF ESTER AND AMIDE DERIVATIVES OF METHAPHOSPHORIC ACID BY PHOTOLYSIS OF 2,3-OXAPHOSPHABICYCLOOCT-5-ENE DERIVATIVES

Irradiation at 254 nm of P-NMe2 and P-OEt derivatives of phosphonates where P is incorporated into the 2,3-oxabicyclooct-ene framework results in fragmentation of the molecules to release N,N-dimethylamino metaphosphoramidate and ethyl metaphophate, respectively.Both species polymerize rapidly, but are effectively trapped as phosphate derivatives when alcohols are included in the reaction mixtures.

FRAGMENTATION REACTIONS OF BRIDGED HETEROCYCLIC PHOSPHORUS COMPOUNDS AS A SOURCE OF LOW-COORDINATION SPECIES

Several types of unsaturated, bridged structures have been prepared that can undergo retro-cycloaddition with the extrusion of phosphorus species having low coordination.By this technique, the species RO-PO2, R-PO2, R2N-P=S, RO-P=S, and R-P=CH2 have been

Diene synthesis with 2-pyrones and 2-pyridones. XXVII. Thermolysis of 1,4-cycloadducts of 2-pyrones with N-phenylmaleimide

It was shown for the first time that the thermolysis of 1,4-cycloadducts of 2-pyrones with N-phenylmaleimide gives either N-phenylimides of 1,2-dihydrophthalic acids or their dimers, depending on the temperature, the heating time, and the structure of the initial adducts.It was established that the N-phenylimides of 1,2-dihydrophthalic acid and 3-bromo-1,2-dihydrophthalic acid dimerize at 196 deg C by a diene synthesis mechanism.