3031-21-8Relevant academic research and scientific papers
Sequential Interaction of Enamine with O, O-Dialkyldithiophosphoric Acid and Electrophilic Reagent
Gazizov, M. B.,Ivanova, S. Yu.,Khairullin, R. A.,Kirillina, Yu. S.,Shamsutdinova, L. P.
, p. 84 - 88 (2020)
The adduct of O, O-dialkyldithiophosphoric acid and enamine reacts exothermically with an electrophilic reagent. In the case of sulfenyl bromide, the iminium salt reduced at the C-Br bond and bis(dialkoxythiophosphorylthio)-disulfide have been formed, experimentally evidencing the reaction of 2-halogenated ald- and ketimines with dithioic acid via the intermediate formation of enamine.
Three component reactions of enamines, O,O-dialkyldithiophosphoric acids, and electrophiles
Gazizov, M. B.,Gazizova, K. S.,Ivanova, S. Yu.,Khairullin, R. A.,Khayarov, Kh. R.,Kirillina, Yu. S.
, (2020)
The product of addition of O, O-dialkyldithiophosphoric acid to enamine reacted with the third reaction component of electrophilic nature, for instance, acetyl chloride, α-bromo ether, or sulfenyl bromide. The reaction involving sulfenyl bromide gave the
Reaction of P(IV) Dithio Acids with N-Alkyl-α-chloroketimines
Khairullin,Gazizov,Kirillina, Yu. S.,Khayarov, Kh. R.,Ivanova, S. Yu.
, (2018)
Effect of the substituent on the imine carbon atom on the result of the reaction of P(IV) dithio acids with N-Alkyl-α-chloroketimines has been studied. New types of ketones containing (O,O-diisopropyl phosphorothioyl)sulfanyl and (diphenylphosphinothioyl)
Bis(O,O-diisopropoxy phosphinothioyl) disulfide - A highly efficient sulfurizing reagent for cost-effective synthesis of oligo (nucleoside phosphorothioate)s
Stec, Wojciech J.,Uznanski, Bogdan,Wilk, Andrzej,Hirschbein, Bernard L.,Fearon, Karen L.,Bergot, B. John
, p. 5317 - 5320 (1993)
A new sulfurizing reagent is reported for the automated synthesis of phosphothioate analogues of oligonucloetides via the phosphoramidite method. Bis(O,diisopropoxy phosphinothioyl) disulfide (S-Tetra, 1) is relatively inexpensive to prepare, easy to handle, and efficiently sulfurizes internucleotide phosphites, thus allowing the practical synthesis of oligo(nucleoside phosphorothioate)s with exceptionally high sulfur content.
Triphenylbismuth(v) di[(iso)nicotinates]-transmetallation agents or divergent organometalloligands? First organobismuth(v)-based silver(i) coordination polymers
Ben Kiran, Ahmad,Mocanu, Teodora,P?llnitz, Alpár,Shova, Sergiu,Andruh, Marius,Silvestru, Cristian
, p. 2531 - 2542 (2018)
The reaction of Ph3BiCl2 with alkali salts of isonicotinic and nicotinic acids afforded Ph3Bi[O(O)CC5H4N-4]2 (1) and Ph3Bi[O(O)CC5H4N-3]2 (2), respectively, which were characterized by multinuclear NMR spectroscopy in solution, mass spectrometry and IR spectroscopy in the solid state. Their molecular structures were established by single-crystal X-ray diffraction. For both 1 and 2 the molecules contain a trigonal bipyramidal C3BiO2 core, with the phenyl groups in equatorial positions. The potential use of 1 and 2 as ditopic organometalloligands was investigated. The reaction of 1 or 2 with Me3SnCl (1:2 molar ratio) resulted in carboxylato ligand exchange and the formation of Me3Sn[O(O)CC5H4N-4] (3) and Me3Sn[O(O)CC5H4N-3] (4) besides Ph3BiCl2. The crystals of both 3 and 4 contain 1-D coordination polymers built through intermolecular N → Sn interactions. The treatment of Ni[S2P(OiPr)2]2 with 1 and 2, respectively, resulted, in addition to di(carboxylato)nickel(ii) derivatives, in isolation of Ph3Bi and the disulphane [(iPrO)2P(S)S]2. New coordination polymers were obtained by reacting 1 and 2 with various silver(i) salts: [Ag{Ph3Bi[O(O)CC5H4N-4]2}(OTf)] (5), [Ag{Ph3Bi[O(O)CC5H4N-3]2}(OTf)]·CH2Cl2 (6·CH2Cl2), [Ag{Ph3Bi[O(O)CC5H4N-4]2}](SbF6)·2THF (7·2THF), [Ag{Ph3Bi[O(O)CC5H4N-3]2}](SbF6)·CH2Cl2 (8·CH2Cl2) and [Ag{Ph3Bi[O(O)CC5H4N-3]2}(NO3)]·CH2Cl2 (9·CH2Cl2). The crystal structures of 5 and 6 can be described as 1-D chains linked by triflate bridges in pairs of chains and 2-D networks, respectively. Compound 7 features a 2-D grid-like topology of the network, with tecton 1 acting as a tridentate ligand through both nitrogen and one oxygen atoms. The linker 2 molecules adopt either cis (compound 6) or trans (compounds 8 and 9) conformation. Complexes 8 and 9 are 1-D chain polymers exhibiting zig-zag and wavy motifs, respectively. The dimensionality of the structures is extended by the presence of supramolecular interactions (π?π, Ag?Ag, Ag?O).
Reactions of the N-isopropyl-α-chloroketimines with PIV dithioacids
Gazizov,Khairullin,Kirillina, Yu. S.,Ivanova, S. Yu.,Khayarov, Kh. R.,Khairullina
, p. 2241 - 2245 (2019/02/07)
A primary iminium salt formed in the reaction of PIV dithioacids with N-isopropyl-α-chloroketimines is transformed into products of nucleophilic substitution of the chlorine atom by dithiophosphorus group (SN pathway), if the imine carbon atom is bonded to the donor and small-volume methyl group, or undergoes reduction of the CCl bond (C-Cl→C-H) (Red pathway), when it is bonded with the bulky acceptor phenyl group. The same effect of substituents was discovered, when replacing methyl group with phenyl one in the position 2 of N-tert-butyl-2-chloraldimines: SN: Red ratio is 1: 0 in the case of Me and 1: 9 in the case of Ph. The iminium salts were transformed into new type ketones containing a phosphor functionality.
Reactions of N-tert-butyl-2,2-dichloro(dibromo)propanimines and O,O-dialkyldithiophosphoric acids
Gazizov, Mukattis B.,Khairullin, Rafail A.,Aksenov, Nikita G.
, p. 272 - 274 (2016/01/12)
The reactions of O,O-dialkyldithiophosphoric acids and N-tert-butyl-2,2-dichloro(dibromo)propanimines initially gave primary iminium salts. These salts subsequently reacted with another two acid molecules resulting firstly in reduction of the C-Hal bond and then nucleophilic substitution of the halogen by the (dialkoxythiophosphorylthio) group. The reactions studied resulted in formation of the reduction-substitution product of the primary iminium salt and bis(dialkoxythiophosphoryl)disulfide.
Reaction of O,O-dialkyldithiophosphoric acid with N-tert-butyl-2,2-dihalopropanimines
Gazizov,Khairullin,Aksenov,Kirillina, Yu. S.,Bandikova, A. Yu.
, p. 1119 - 1121 (2017/01/13)
O,O-Dialkyldithiophosphoric acid reacted with N-tert-butyl-2,2-dihalopropanimines to give iminium salt as a primary product, which further sequentially undergoes reaction with two equivalents of dithiophosphoric acid to initially reduce the C—X (X = Cl, Br) bond in the iminium salt and then nucleophilic replacement of the halogen atom with dialkoxydithiophosphate group. The final reaction products are the reduction—substitution product of the primary salt and bis(dialkoxythiophosphoryl) disulfide.
Reactions of O,O-dialkyldithiophosphoric acids with N-tert-butyl-2-bromo-2-methylpropanimine and its salts
Gazizov, Mukattis B.,Khairullin, Rafail A.,Aksenov, Nikita G.,Sinyashin, Oleg G.
, p. 4993 - 4996 (2015/08/04)
Abstract The reactions of O,O-dialkyldithiophosphoric acids with N-tert-butyl-2-bromo-2-methylpropanimine and its salts resulted in reduction of the carbon-bromine bond in the iminium salt giving bis(dialkoxythiophosphoryl)disulfide and N-tert-butyl-2-methylpropaniminium bromide. This represents the first example of C-Br bond reduction by O,O-dialkyldithiophosphoric acids.
Reaction of O,O-dialkyldithiophosphoric acids with N-alkyl-2-haloaldimines
Khairullin,Gazizov,Aksenov,Khayarov, Kh. R.
, p. 2099 - 2105 (2015/10/29)
Synthetic results of reactions of O,O-dialkyldithiophosphoric acids with N-alkyl-2-haloaldimines fundamentally depend on the nature of the halogen: in the case of Cl-substituted imines the reaction afforded 2-(dialkoxythiophosphorylthio)iminium chlorides, with bromoimines bis(dialkoxythiophosphoryl) disulfide and unsubstituted iminium bromide were obtained. According to dynamic 31P NMR spectroscopy data the reason for this difference is the presence or absence of a free acid in the reaction medium.
