1056-25-3Relevant articles and documents
An easy one-pot procedure for the synthesis of N-sulfonyl phosphorous ylides and sulfonyl iminophosphoranes
Shaabani, Ahmad,Rahmati, Abbas,Naderi, Soheila
, p. 553 - 557 (2007)
Reaction of triphenylphosphine and an electron deficient acetylenic ester in the presence of strong N-H acid such as alkyl and aryl sulfamides or acetamide produces phosphorous ylides at room temperature in CH 2Cl2. The aryl sulfamide phosphoranes undergo a smooth transformation reaction in boiling toluene and produce iminophosphoranes. Springer-Verlag 2007.
Synthesis of sulfur-containing aryliminophosphoranes
Yavari, Issa,Zabarjad-Shiraz, Nader,Bijanzadeh, Hamid R.
, p. 1381 - 1386 (2004)
Stabilized phosphoranes, obtained from the three-component reaction between dialkyl acetylenedicarboxylates and arylsulfonamides in the presence of triphenylphosphine, undergo a smooth intramolecular reaction, in boiling toluene to produce sulfur-containing iminophosphoranes in excellent yields.
Self-propagating high-temperature synthesis in the solid-phase triphenylphosphine-chloramine system
Klimchuk, E. G.,Khodak, A. A.,Merzhanov, A. G.
, p. 300 - 304 (1999)
The macrokinetics and products of self-propagating high-temperature synthesis (SHS) in the solid-phase triphenylphosphine-chloramine system were studied by TGA-DTA, XRD, and 31P NMR techniques. The temperature of SHS ignition (59 deg C), the velocity of reaction waves (1.6-5.0 nm s-1), and the maximum temperature (155-239 deg C) in the SHS wave were measured. The chemical composition of the product obtained was established: phosphine oxide, triphenyl-N-(phenylsulfoyl)-phosphinimine, benzenesulfonamide, NaCl, and water. The scheme of chemical reactions occurring during SHS was proposed.
Copper-catalyzed imination of sulfoxides and sulfides
Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
supporting information, p. 4697 - 4702 (2019/07/22)
Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
Hypervalent iodine in synthesis XXXI: Formation of phosphinimines and arsinimines by nitrene route or non-nitrene route
Ou, Wei,Wang, Zhi-Gang,Chen, Zhen-Chu
, p. 2301 - 2309 (2007/10/03)
N-sulfonyltriphenylphosphinimines and N-sulfonyltriphenylarsinimines are prepared by the reaction of triphenylphosphine or triphenylarsine under nitrene-producing conditions with I-N ylide (PhI=NSO2R). Triphenylarsinimines can also be generated by a non-nitrene route from triphenylarsine, iodobenzene diacetate, and sulfonamides via triphenylarsine diacetate, Ph3As(OAc)2.
Synthesis of N-Acyl-, N-Sulfonyl-, and N-Phosphinylphospha-λ5-azenes by a Redox-Condensation Reaction Using Amides, Triphenylphosphine, and Diethyl Azodicarboxylate
Bittner, Shmuel,Assaf, Yonit,Krief, Penina,Pomerantz, Martin,Ziemnicka, Barbara T.,Smith, Christina G.
, p. 1712 - 1718 (2007/10/02)
The reaction of phosphines and amides with diethyl azodicarboxylate (DAD) produced phospha-λ5-azenes.Thus aromatic amides and those aliphathic amides with electron-withdrawing substituents gave N-acyl-P,P,P-triphenylphospha-λ5-azenes (5) when triphenylphosphine (TPP) was employed.Both aryl- and alkylsulfonamides reacted with TPP and DAD to produce the N-sulfonylphospha-λ5-azenes (9).Diphenylphosphinamide (10) and ethyl carbamate (12) also produced the respective phosphazenes (11 and 13) with TPP and DAD.Secondary carboxamides and sulfonamides did not react with TPP and DAD.The reaction of triethyl phosphite with sulfonamides in the presence of DAD produced the phosphorimidates (20) in an analogous reaction, along with the corresponding N,N-diethylsulfonamides and the deethylated adduct of triethyl phosphite and DAD (23).Triethyl phosphite-DAD failed, however, to give a phosphorimidate with carboxamides but gave, instead, the rearranged adduct of DAD and triethyl phosphite (19).Tris(dimethylamino)phosphine reacted with sulfonamides and DAD but the products were the corresponding ethyl N-sulfonylcarbamates (26) rather than the phosphazenes.Tris(dimethylamino)phosphine reacted with azodicarbonamide (a molecule which contains both the azo and carboxamide groups) with the production of N,N-dimethylurea, again without formation of the phosphazene.Finally, the reaction of triphenylarsine with benzenesulfonamide and DAD produced N-(phenylsulfonyl)triphenylarsa-λ5-azene (30) but triphenylstibene with DAD and benzenesulfonamide only gave triphenylstibene oxide.Mechanistic possibilities for these reactions are also discussed.
REACTION OF N-SUBSTITUTED N'-ACYLSELENIUM DIIMIDES WITH OLEFINS
Derkach, N. Ya.,Barashenkov, G. G.,Levchenko, E. S.
, p. 1435 - 1438 (2007/10/02)
N-Substituted N'-acylselenium diimides, which contain a Se=N-C=O group, react with olefins by a 1,4-cycloaddition mechanism with the formation of the corresponding substituted 4-imino-5,6-dihydro-4,1,3-selenaoxazines.
