- N,N′-dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): An efficient reagent for the synthesis of chemical weapons convention-related dialkyl-N,N-dialkylphosphoramidates from dialkylphosphites
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The present paper describes the one-pot synthesis of dialkyl N,N-dialkylphosphoramidates (DADAP) from dialkylphosphites and dialkylamines using N,N?-dichlorobis(2,4,6-trichlorophenyl)urea (CC-2) as chlorinating reagent. DADAP belong to the schedule 2.B.6 category of the Chemical Weapons Convention (CWC), as they are the important markers of the chemical warfare agent tabun and its analogues. The study was undertaken to develop the spectral database of DADAP for verification of CWC. The reported synthetic strategy can be adopted to rapidly synthesize several analogues of DADAP during official proficiency tests. CSIRO 2007.
- Gupta, Arvind K.,Pardasani, Deepak,Gupta, Hemendra K.,Dubey, Devendra K.
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- Dichlorodimethyl hydantoin: An efficient reagent for one-pot synthesis of CWC-related O,O-dialkyl, N,N-dialkyl phosphoramidates
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A simple, rapid, economical, and efficient one-pot synthetic method for preparation of O,O-dialkyl, N,N-dialkylphosphoramidates (DADAPs) and phosphates has been developed. Copyright Taylor & Francis Group, LLC.
- Gupta, Arvind K.,Dubey, Devendra K.,Kaushik
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- DIALKYLAMINO GROUP TRANSFER FROM TITANIUM (IV) TO PHOSPHORYL CENTRE. STRUCTURE-REACTIVITY STUDIES
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Reaction between phosphoryl substrates, (EtO)2P(O)X (X = H, R, OR) and dialkylaminoderivatives of Ti(IV), Ti(NR2)nCl4-n and Mn(NEt2)2 leads to the exchange of one or both EtO groups for the NR2 substituent.The reactivity of the system depends on electronic, as well as steric, effects of both substrates, and approximately correlates with the Lewis acid-base interaction between the substrates, as measured by the i.r. spectroscopy.
- Froneman, M.,Cheney, D. L.,Modro, T. A.
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p. 273 - 281
(2007/10/02)
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- PERACID AND ACYL PEROXY RADICAL MEDIATED OXIDATION AND REARRANGEMENT OF PHOSPHORAMIDES
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Acyl peroxy radicals can cause oxidation of sulphur at pentavalent phosphorus and can also affect the decomposition of phosphoramides.Peracids can also oxidise thiophosphorus compounds to their respective oxidised phosphorus analogues and oxidise phosphoramides via N-oxidation.
- Davidson, R. Stephen,Walker, Martin D.
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p. 305 - 310
(2007/10/02)
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- DIRECT TRANSFORMATION OF PHOSPHINIC ACIDS IN THE 3-PHOSPHOLENE SERIES TO PHOSPHINAMIDES
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Tris(N,N-dialkylamino)phosphines undergo a transamination reaction with phosphinic acids containing the 3-phospholene ring.Yields of phosphinamides ranged from 66 to 93percent for five different combinations.Products were characterized by 13C and 31P NMR.Transamination was not effected with diphenylphosphinic acid or methylphosphonic acid, but a low conversion of diethyl phosphate to its amide was achieved.With p-toluenesulfonic acid, tris(N,N-dimethylamino)phosphine was converted to a stable salt.The mechanism of the reaction with the phospholene acids was determined by 31P NMR studies to proceed through formation of a mixed anhydride R2P(O)-O-P(NR'2)2; the displaced dialkylamino group then attacks at phosphoryl to give the phosphinamide.
- Szewczyk, Jerzy,Lloyd, John R.,Quin, Louis D.
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p. 155 - 160
(2007/10/02)
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- Electroorganic Chemistry. 81. Anodic Oxidation of Sulfonamides and Amidophosphates
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Oxidation peak potentials of sulfonamides and amidophosphates were measured in acetonitrile and compared with the corresponding amides and carbamates.The results showed that the order of easiness of oxidation was amides > carbamates > amidophosphates > sulfonamides.Furthermore, the reaction of silyl enol ethers or trimethyl phosphite with anodically α-methoxylated sulfonamides or amidophosphates has clearly shown that the α-methoxylated compounds are useful starting materials in organic synthesis.For example, optically active L-tryptophan was synthesized from α-methoxylated N-(p-tolylsulfonyl)-L-proline ester.
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Uchida, Kenshi,Kanazawa, Takenobu,Tsuda, Kunio
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p. 3711 - 3716
(2007/10/02)
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- SOLVOLYSIS OF DIPHENYL AMIDOPHOSPHATES IN AQUEOUS ALCOHOLIC MEDIA
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Influence of substituent on the reaction rate of the alkali-catalyzed solvolysis of the studied compounds set has been followed.The activation entropy has also been determined.The reaction products have been identified, and their concentration ratio has been determined.The reaction selectivity is mostly influenced by sterical effects in the substrate molecule.The results obtained agree with the SN2 mechanism.
- Kasparek, Frantisek,Mollin, Jiri
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p. 386 - 396
(2007/10/02)
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