- Direct Conversion of Diethyl Hydrogen Phosphate into Diethyl Phosphoramides
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The effective, one-step transformation of diethyl hydrogen phosphate into diethyl phosphoramides by using hexamethyltriaminodibromophosphorane prepared "in situ" is described. - Keywords: Hexamethyltriaminodibromophosphorane; Intermolecular dehydration
- Zwierzak, Andrzej,Osowska-Pacewicka, Krystyna
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- [{ReH2(PMePH2)2}2(μ-H) 3]-: The first member of a new class of anionic polyhydride dimers [Re2H7L4]-
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[K(Q)][{ReH2(PMePh2)2}2(μ-H) 3] is prepared by treatment of {ReH2(PMePh2)2}2)μ-H) 4 with potassium hydride and a crown ether (Q = 18-crown-6 or 1,10-diaza-18-crown-6). The [K(1,10 diaza-18-crown-6)]+ salt contains NH···HRe protonic - hydridic bonds and has been characterized by 31P NMR, variable temperature 1H NMR, IR, and X-ray crystallography. The pKαTHF = 33 of {ReH2(PMePh2)2}2(μ-H) 4 was determined on the basis of its reaction with [K(2,2,2-crypt)][PO(OEt)2NPh.
- Hinman,Abdur-Rashid,Lough,Morris
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- The Step-Wise Synthesis of Oligomeric Phosphoramidates
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In this study, the step-wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N?P?N, symmetric and asymmetric P?N?P and P?N?P?N?P linkages. Salt elimination and lithiation strategies were employed to create the new P?N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P?N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.
- Data, Shailja,Leung Wai, Jeffery,Kumar, Saawan,Cameron, Alan J.,Trehet, Manon,Itumoh, Emeka J.,Feld, Joey,S?hnel, Tilo,Leitao, Erin M.
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supporting information
p. 5468 - 5477
(2021/09/30)
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- Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
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A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.
- Xu, Pan,Zhong, Zijian,Zhou, Aihua
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supporting information
p. 5342 - 5347
(2021/06/30)
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- Evaluation and development of methodologies for the synthesis of thiophosphinic acids
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Thiophosphorus acids R1R2P(S)OH constitute an important class of organophosphorus compounds, in which the phosphorus atom is intrinsically chiral if R1 ≠ R2. In connection with a project aimed at the preparation of chiral thiophosphorus acids, various available literature methods were considered, but few fit the requirement of odorless reagents. Herein, the results of our studies on the synthesis of thiophosphinic acids are reported. Ultimately, two major approaches were selected: (1) the Stec reaction of phosphorus amides with carbon disulfide; and (2) the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur. An application to the preparation of a potential chiral phosphorus organocatalyst is also reported.
- Winters, Karen R.,Montchamp, Jean-Luc
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p. 14545 - 14558
(2020/12/29)
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- Synthesis of N-Substituted phosphoramidic acid esters as “reverse” fosmidomycin analogues
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An efficient synthetic pathway to a series of novel “reverse” fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial “pro-drugs”.
- Adeyemi, Christiana M.,Hoppe, Heinrich C.,Isaacs, Michelle,Klein, Rosalyn,Lobb, Kevin A.,Kaye, Perry T.
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p. 2371 - 2378
(2019/03/23)
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- On the rearrangement of N-aryl-N-Boc-phosphoramidates to N-Boc-protected o-aminoarylphosphonates
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Abstract: Various arylamines were converted in two steps to N-Boc-N-arylphosphoramidates. LiTMP and LDA induced directed ortho-metalation at temperatures from ?78 to 0?°C. The ensuing [1,3]-migration of the phosphorus atom with its substituents from the n
- Kuliszewska, Edyta,Hammerschmidt, Friedrich
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- Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR)3 and its synthetic applications
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A systematic study on the iodine-mediated phosphoramidation reaction of amines and trialkyl phosphites was conducted, which not only disclosed the factors affecting the reaction but also revealed that it could proceed smoothly in CH2Cl2 at room temperature in open air. Using this method, various phosphoramidates with different aliphatic amines and aromatic amines were synthesized in good to excellent yields. Our present investigation shows that this underused method is actually a mild, practical and general way to synthesize phosphoramidates and will have wide applications.
- Chen, Xunwei,Xiao, Zecai,Chu, Hanyu,Wang, Bo,Peng, Ai-Yun
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p. 6783 - 6790
(2018/09/29)
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- Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate
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A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.
- Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
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supporting information
p. 4938 - 4941
(2018/08/24)
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- Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton-Todd Reaction under Base-Free Conditions
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A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton-Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.
- Kaboudin, Babak,Donyavi, Atousa,Kazemi, Foad
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p. 170 - 174
(2017/09/28)
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- Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton-Todd reaction Dedicated to Professor Tsutomu Yokomatsu from Tokyo University of Pharmacy and Life Sciences on the occasion of his 65th birthday
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A simple and efficient method is presented for the synthesis of phosphoroamidates in moderate to good yield via the Atherton-Todd coupling of primary amines with H-dialkyl phosphites using Fe3O4@MgO nanoparticles as a recyclable catalyst.
- Kaboudin, Babak,Kazemi, Foad,Habibi, Fereshteh
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supporting information
p. 6364 - 6367
(2015/11/16)
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- New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles
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Benzotriazole surrogates showing higher stabilities than the corresponding chlorophosphates, allow phosphonylation of a variety of N-, O-, and S-nucleophiles in good yields.
- Panmand, Deepak S.,Tiwari, Anand D.,Panda, Siva S.,Monbaliu, Jean-Christophe M.,Beagle, Lucas K.,Asiri, Abdullah M.,Stevens, Christian V.,Steel, Peter J.,Hall, C. Dennis,Katritzky, Alan R.
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supporting information
p. 5898 - 5901
(2015/01/08)
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- Iodine catalyzed solvent-free cross-dehydrogenative coupling of arylamines and H-phosphonates for the synthesis of N-arylphosphoramidates under atmospheric conditions
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Aerobic oxidative coupling of various arylamines and H-phosphonates to the corresponding N-arylphosphoramidates has been achieved under solvent-free conditions using molecular iodine. This protocol works at room temperature furnishing the corresponding P-
- Dar, Bashir Ahmad,Dangroo, Nisar A.,Gupta, Amit,Wali, Aarti,Khuroo, Mohammad Akbar,Vishwakarma, Ram A.,Singh, Baldev
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p. 1544 - 1548
(2014/03/21)
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- Phosphoramidate tantalum complexes for room-temperature C-H functionalization: Hydroaminoalkylation catalysis
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A cooled reaction: Phosphoramidate-ClTaMe3 complexes promote the first example of room-temperature hydroaminoalkylation catalysis. This reaction can be realized under solvent-free conditions and with challenging substrates such as styrenes and dialkyl amines. When using a vinylsilane substrate, for the first time the linear regioisomer is obtained preferentially using a Group5 metal. TBS=tert-butyldimethylsilyl, TMS=trimethylsilyl. Copyright
- Garcia, Pierre,Lau, Ying Yin,Perry, Mitchell R.,Schafer, Laurel L.
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p. 9144 - 9148
(2013/09/12)
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- Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates
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The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.
- Fraser, Jamie,Wilson, Laura J.,Blundell, Rebecca K.,Hayes, Christopher J.
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supporting information
p. 8919 - 8921
(2013/09/24)
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- Kinetics and mechanism of the anilinolysis of dibutyl chlorophosphate in acetonitrile
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The nucleophilic substitution reactions of dibutyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.86-0.97) with the strongly basic anilines while primary normal (kH/kD = 1.04-1.10) with the weakly basic anilines. The DKIEs, steric effects of the two ligands, activation parameters, cross-interaction constants, variation trends of the kH/kD values with X, and mechanism are discussed for the anilinolyses of the nine (R1O)(R2O)P(=O)Cl-type chlorophosphates. A concerted mechanism is proposed with a backside nucleophilic attack transition state for the strongly basic anilines and with a frontside attack involving a hydrogen-bonded four-center-type transition state for the weakly basic anilines on the basis of the magnitudes, secondary inverse and primary normal, and variation trends of the kH/kD values with X.
- Hoque, Md. Ehtesham Ul,Lee, Hai Whang
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scheme or table
p. 663 - 669
(2012/05/19)
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- Kinetics and mechanism of the anilinolysis of dibutyl chlorothiophosphate in acetonitrile
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The nucleophilic substitution reactions of dibutyl chlorothiophosphate (4S) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are primary normal (k H/kD = 1.10-1.35). A concerted mechanism involving predominant frontside nucleophilic attack is proposed on the basis of the primary normal DKIEs and selectivity parameters. Hydrogen bonded, four-center-type transition state is proposed. The steric effects of the two ligands on the anilinolysis rates of the chlorothiophosphates are discussed. The anilinolyses of P=S systems are compared with those of their P=O counterparts on the basis of the reactivities, thio effects, selectivity parameters, and DKIEs.
- Ul Hoque, Md. Ehtesham,Lee, Hai Whang
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experimental part
p. 843 - 847
(2012/06/01)
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- Kinetics and mechanism of anilinolysis of phenyl n-phenyl phosphoramidochloridate in acetonitrile
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The kinetic studies on the reactions of phenyl N-phenyl phosphoramidochloridate (8) with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) have been carried out in acetonitrile at 60.0 oC. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are huge secondary inverse (kH/kD = 0.52-0.69). A concerted mechanism is proposed with a backside attack transition state (TS) on the basis of the secondary inverse DKIEs and the variation trends of the kH/kD values with X. The degree of bond formation in the TS is really extensive taking into account the very small values of the DKIEs. The steric effects of the two ligands on the rates are extensively discussed for the aminolyses of the chlorophosphate-type substrates on the basis of the Taft equation.
- Ul Hoque, Md. Ehtesham,Lee, Hai Whang
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p. 3274 - 3278
(2013/01/15)
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- Kinetics and mechanism of the anilinolysis of diisopropyl chlorophosphate in acetonitrile
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The nucleophilic substitution reactions of diisopropyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 oC. The anilinolysis rate of 3 is rather slow to be rationalized by the conventional stereoelectronic effects. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.71-0.95) with maximum magnitude at X = H. A concerted mechanism involving predominant backside nucleophilic attack is proposed on the basis of the secondary inverse DKIEs.
- Ul Hoque, Md. Ehtesham,Lee, Hai Whang
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scheme or table
p. 3245 - 3250
(2012/01/17)
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- Practical and reliable synthesis of dialkyl N-arylphosphoramidates with nitroarenes as substrates
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A new single-step transformation of readily available nitroarenes with trialkyl phosphites, which can be performed both under thermal and microwave conditions, delivers dialkyl N-arylphosphoramidates in good yields and short reaction times.
- Haggam, Reda,Conrad, Jürgen,Beifuss, Uwe
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scheme or table
p. 6627 - 6630
(2010/03/01)
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- Chemoselective staudinger-phosphite reaction of azides for the phosphorylation of proteins
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The title reaction was identified as a chemoselective means to modify azides in peptides and proteins in high yields at room temperature in various solvents including aqueous buffers at physiological pH. In combination with nonnatural protein translation
- Serwa, Remigiusz,Wakening, Lna,Signore, Giuseppe Del,Muehlberg, Michaela,Claussnitzer, Iris,Weise, Christoph,Gerrits, Michael,Hackenberger, Christianr P. R.
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supporting information; experimental part
p. 8234 - 8239
(2010/01/16)
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- Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates
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The deuterium kinetic isotope effects (KIEs) involving deuterated aniline nucleophiles (XC6H4ND2) are reported for the reactions of dimethyl chlorophosphate (1), dimethyl chlorothionophosphate (2), diethyl chlorophosphate
- Dey, Nilay Kumar,Hoque, Md. Ehtesham Ul,Kim, Chan Kyung,Lee, Bon-Su,Lee, Hai Whang
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scheme or table
p. 544 - 548
(2009/04/04)
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- The phosporylation of aniline derivatives in biphase systems
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Aniline derivatives were phosphorylated in biphase systems using three methods. A comparative study was performed. The best results were obtained when a solid-liquid system was used. This method is the easiest and lead to higher yields (54-81%). Copyright
- Ilia, Gheorghe,Petric, Mihaela,Macarie, Lavinia,Iliescu, Smaranda,Popa, Adriana
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p. 1717 - 1723
(2007/10/03)
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- Iodoform, a New Reagent in the Todd-Atherton Reaction
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An innovative and convenient application of the iodoform (1) as the reagent in the synthesis of phosphoramidates via Todd-Atherton reaction is described. The full stereoselectivity of this transformation using a 4-methyl-1,3,2-dioxaphosphinane model system was demonstrated.
- Mielniczak, Grazyna,Lopusinski, Andrzej
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p. 3851 - 3859
(2007/10/03)
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- Synthesis and some transformations of (dialkoxy)arylimidophosphinoylformamidines
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Dialkyl hydrogen phosphites add reversibly to dicyclohexylcarbodiimide, forming N,N'-dicyclohexylformamidines.Similar addition products derived from phenylphophoramidites and diphenylcarbodiimide are converted on heating or on prolonged storage at room temperature into 1-dialkoxyphosphino-1,2,3-triphenylguanidines together with other products; their hydrolysis gives anilidophosphates and diphenylformamidine, and under the action of dithiophosphoric acids they lose both alkyl groups, yielding zwitterionic anilido(formamidinio)phosphonates.
- Kamalov, R. M.,Khailova, N. A.,Al'fonsov, V. A.,Pudovik, M. A.
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- The synthesis of ascididemin
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A short synthsis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2- iodoaniline and triethylaluminium, followed by oxidation with barium manganate.
- Moody, Christopher J.,Rees, Charles W.,Thomas, Robert
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p. 3589 - 3602
(2007/10/02)
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- THIONO COMPOUNDS. 9. USE OF SPECTRA TO STUDY INTERMEDIATES IN THE OXIDATION OF THIONO PHOSPHORUS COMPOUNDS
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Intermediates in the oxidation by m-chloroperoxybenzoic acid (MCPBA) of 13 structurally different thiophosphoramides and phosphorothioates were studied at -25 deg C to 0 deg C using NMR, EPR, UV, IR and Raman spectra.The lifetimes of intermediates ascertained by NMR varied from a few minutes to many hours at the same temperature and were longer for thiono esters than for amides, for aryl than for alkyl constituents, and for electron-donating substituents on aryl groups than for electron-withdrawing groups.The major 31P NMR peaks for all intermediates appeared in the same region, about midway between the resonances of the P(S) starting materials and the P(O) products, indicating close structural similarly to one another for the intermediates; the range of 13-33 ppm for the major peaks indicates that the intermediates are tetracoordinate and supports phosphonium polysulfide structures for them of the type R3PSx (26, Scheme 1), or perhaps R3POSx.UV spectra also afforded support for polysulfide structures, since typical absorption develops and then disappears.Raman, 31P NMR, and UV spectra are consistent with longer-term presence of bisphosphonium species (e.g. 25, from reactions of 26; Scheme 1).EPR spectra gave no indication of homolysis. - Key words: Phosphorothioates, Raman Spectra, Infrared Spectra, Thionophosphorus, NMR Spectra, Thiophosphoramides
- Swinson, Joel,Field Lamar,Heimer, Norman E.,Michalska, Danuta,Muccio, Donald D.,et al.
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p. 159 - 172
(2007/10/02)
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- A New Approach to the Atherton-Todd Reaction
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N-Arylphosphoramidates 4 are prepared by reacting formanilides 1 and chloroacetanilides 1' with diethyl phosphite under phase-transfer conditions.
- Lukanov, L. K.,Venkov, A. P.,Mollov, N. M.
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p. 971 - 973
(2007/10/02)
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- Anhydrides of Phosphorus and Sulfur Acids, 2. Mixed Anhydrides of Phosphoric, Phosphonic, and Phosphinic Acids with Sulfonic Acids and Sulfuric Monoimidazolide. New Methods of Synthesis, Novel Structures, Phosphorylating Properties
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New applications of methods leading to anhydrides RR'P(O)OSO2R'' (1) are described: a) Reaction of acids RR'P(O)OH (2) with sulfonic imidazolides. b) Reaction of phosphorus imidazolides 4 with sulfonic acids and sulfonic anhydrides.New methods of synthesis of anhydrides 1 have been developed. c) Reaction of phosphorus acid silyl esters RR'P(O)OSiMe3 (9) with methanesulfonic and trifluoromethanesulfonic anhydrides. d) Reaction of bis(trimethylsilyl) tert-butylphosphonate (10) with methanesulfonic acid leading to tBuP(O)(OSO2Me)2 (11). e) Reaction of stannyl phosphate (EtO)2P(O)OSnMe3 (15) with methanesulfonic anhydride. f) Reaction of phosphorus acid silyl esters 9 with trimethylsilyl trifluoromethanesulfonate.All methods result in high yields and can be adapted to a variety of anhydrides 1 derived from phosphoric, phosphonic, and phosphinic acids on the one hand and methanesulfonic, trifluoromethanesulfonic acids and sulfuric monoimidazolide on the other.Phosphonium intermediates have been demonstrated by low temperature FT 31P NMR spectroscopy for reaction b) and c).The anhydrides 1 are readily converted into imidazolides 4 by the reaction with N-(trimethylsilyl)imidazole which proceeds via two distinct phosphonium intermediates.With neutral and weakly basic nucleophiles, the anhydrides 1 behave as phosphorylating agents.
- Dabkowski, Wojciech,Michalski, Jan,Skrzypczynski, Zbigniew
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p. 1809 - 1824
(2007/10/02)
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- ON THE REACTION OF PHOSPHORUS ACID ESTERS WITH NUCLEOPHILES IN THE PRESENCE OF CARBON TETRACHLORIDE
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Esters of N-Phosphoryl phosphazenes are prepared by a modified Atherton-Todd reaction from di- and triesters of phosphorous acid, sodium azide, and carbon tetrachloride in high yields.The utilization of the two-component system trialkyl phosphite/ carbon tetrachloride for preparing phosphazenes, (RO)3P=NY (Y: PO(OR)2, SO2R, COR, CN), and dialkoxyphosphoryl compounds, (RO)2P(O)X (X: NHR, NR2, OPh, CN, F, NCO), is presented.
- Riesel, Lothar,Herrmann, Eckhard,Steinbach, Joerg
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p. 253 - 258
(2007/10/02)
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- THE APPLICATION OF DIALKYLPHOSPHITE AS THE AMINO PROTECTION REAGENT IN ORGANIC SYNTHESIS
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The acid hydrolysis of N-phenyl-N-dialkyl-phosphoramidates was studied by HPLC, the N-phenyl-N-diisopropylphosphoramidate has half life 53 min in 6N HCl at 50 deg C.The P-N bonds of these phosphoryl derivatives also show a relative stability in organic and Lewis acids.
- Zhao, Yu-Fen,Ji, Gai-Jiao,Xi, She-Kang,Tang, Hue-Gong,Song, Ai-Teng,Wei, Shou-Zuo
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p. 155 - 158
(2007/10/02)
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- Phosphoric and Phosphinic Sulfonic Anhydrides - Reinvestigation and Corrections. Novel Methods of Synthesis
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Earlier works from this and other laboratories on phosphoric and phosphinic sulfonic anhydrides have been reinvestigated.It was found that no single reaction described in the past provides a general method for the production of mixed anhydrides RR'P(O)SO2R'' (3) in high yields of isolated products.The following three efficient synthetic procedures leading to pure anhydrides 3 are described: a) Trifluoromethanesulfonic acid promoted reaction of phosphinic acid 9 with sulfonic triazolides 10. b) Reaction of phosphinic and phosphoric imidazolides 13 with sulfonic acid 6. c) Reaction of 13 with sulfonic anhydride 15.All methods result in high yields.Some chemical properties of the anhydrides 3 are described.
- Dabkowski, Wojciech,Michalski, Jan,Radziejewski, Czeslaw,Skrypczynski, Zbigniew
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p. 1636 - 1643
(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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