Reactions of organotin compounds. X. Reactions of tin hydrides with CF2=CFRe(CO)5, CF3CF=CFRe(CO)5, and some fluorinated alkenes

1969 ◽  
Vol 47 (20) ◽  
pp. 3753-3758 ◽  
Author(s):  
M. Akhtar ◽  
H. C. Clark

Trimethyltin hydride reacts with CF2=CFRe(CO)5 under ultraviolet irradiation to give new fluorovinyl derivatives of —Re(CO)5. Similar products were obtained using dimethyltin dihydride, but no reaction occurred between trimethyltin hydride and CF3CF=CFRe(CO)5. The reactions of trifluoroethylene, 1,1-difluoroethylene, and vinyl fluoride with trimethyltin hydride have been studied, thus completing the sequence of such reactions with fluorinated ethylenes. While both possible addition products were obtained with trifluoroethylene, and also from the corresponding reaction with perfluoropropene, 1,1-difluoroethylene gave only (CH3)3SnCH2CF2H, and with vinyl fluoride only trimethyltin fluoride and ethylene were isolated. Possible explanations are proposed and spectroscopic data for the new compounds are presented.

1979 ◽  
Vol 34 (1) ◽  
pp. 31-43 ◽  

Abstract Tetramethyldiphosphinomethane (CH3)2PCH2(CH3)2 (1a) reacts with HCl/ether to form the mono-and bisquaternary salts [(CH3)2PCH2P(H)(CH3)2]Cl (2) and [(CH3)2(H)PCH2P(H)(CH3)2]Cl2 (3), respectively. The system 1a/HCl, incorporating 1 a/2/3, represents a useful tool for studying the appearance of XnAA′X′n-spin type systems. These compounds are also prototypes for a variety of other mono-or bis-phosphonium salts, which are formed in the reactions of the diphosphines (CH3)2PCH2PR2 (R = CH3, t-C4H9, C6H5) (1a-c) with (CH3)2CO + HCl, CH3I, t-C4H9Br, C6H5COCl, (CH3)2PCl and Br(CH2)nBr (n = 1, 2). Heterocycles are not obtained. The dioxide 14 and the disulfide 15 are also described. Some properties and spectroscopic data (IR, 1H, 31P and 13C NMR) of 26 new compounds are reported and briefly discussed.


1968 ◽  
Vol 46 (12) ◽  
pp. 2165-2173 ◽  
Author(s):  
M. Akhtar ◽  
H. C. Clark

The formation of addition products (CH3)3MCFHCF2Sn(CH3)3 and (CH3)3MCF[Sn(CH3)3]CF2H where M = Ge or Sn has been observed in reactions involving the ultraviolet irradiation of (CH3)3MCF=CF2 with trimethyltin hydride. The former type of addition product is more stable than the latter, and the stability of both types decreases in the order M = Si, Ge, or Sn. Evidence is presented that decomposition occurs in all cases by a β-fiuorine elimination with the formation of fluorovinyl derivatives of M and trimethyltin fluoride. Similar reactions occur between (CH3)3GeCF=CF2 and dimethyltin dihydride and between (CH3)2Ge(CF=CF2)2 and dimethyltin dihydride or trimethyltin hydride. The evidence indicates that a free radical process is involved. Spectroscopic data are presented for new organogermanium compounds.


1968 ◽  
Vol 46 (4) ◽  
pp. 633-642 ◽  
Author(s):  
M. Akhtar ◽  
H. C. Clark

The reactions of trimethyltin hydride and dimethyltin dihydride with (CH3)3SiCF=CF2 and (CH3)2Si(CF=CF2)2 respectively have been investigated. Under thermal conditions, reaction led to organotin fluorides and fluorovinyl-silanes. However, under ultraviolet irradiation at 25°, addition products were isolated of which (CH3)3SiCFHCF2Sn(CH3)3 and (CH3)3SiCF[Sn(CH3)3]CF2H were fully characterized. Evidence is presented which shows that these addition products are formed by a free radical process and that their decomposition to organotin fluorides and fluorovinyl-silanes proceeds via a β-fluorine elimination. Spectroscopic data are presented for a number of new organo-silanes.


1985 ◽  
Vol 40 (9) ◽  
pp. 1173-1176 ◽  
Author(s):  
E. N. Sakuntala ◽  
E. N. Vasanta

Reactions of tin tetraacetate with various bifunctional tetradentate Schiff bases have been carried out in refluxing toluene (with the azeotropic removal of the liberated acetic acid) in 1:1 and 1:2 molar ratios. But only the diacetate derivatives of tin have been isolated as stable monomeric compounds. Benzoxazine, a potentially bifunctional tetradentate ligand, is found to undergo a rearrangement when reacted with tin tetraacetate as well as with organotin compounds. All the new compounds are characterised by NMR and IR spectral data.


1987 ◽  
Vol 42 (8) ◽  
pp. 984-992 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Jürgen Nientiedt

AbstractThe reactions of F3CP = CF2 (1) with Me3GeH, Me3SnH, and (C5R5)(CO)3MH (M = Cr. Mo, W; R = H , Me) proceed via addition to the PC double bond yielding tertiary phosphanes of the type Me3M′P(CF3)CF2H[M′ = Ge (2), Sn (3)] or (C5R5)(CO)3MP(CF3)CF2H [R = H; M - Cr (6), Mo (7). W (8); R = Me; M = Mo (9), W (10)]. 2 and 3 are labile compounds, which decompose by elimination of Me3M′F , a reaction which in the case of 3 has been used to prepare the new phosphaalkene F3CP = C(H)F (5) and its [2+4]-cycloaddition product 4 with 2.3-dimethyl-1.3- butadiene. The H substituent (instead of F) in 5 and its derivatives has a surprising influence not only on the stability of the compounds but also on their spectroscopic data, as shown by com parison with 1 and derivatives of the type Me3M ′P(CF3)2 and (C5H5)(CO)3MP(CF3)2. respectively. New compounds are characterized by NMR, MS. GC/MS and IR measurements.


2020 ◽  
Vol 5 (443) ◽  
pp. 85-91
Author(s):  
Ibrayev M.K., ◽  
◽  
Takibayeva A.T., ◽  
Fazylov S.D., ◽  
Rakhimberlinova Zh.B., ◽  
...  

This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.


2020 ◽  
Vol 17 ◽  
Author(s):  
Rahele Bargebid ◽  
Ali Khalafi-Nezhad ◽  
Kamiar Zomorodian ◽  
Leila Zamani ◽  
Ali Ahmadinejad ◽  
...  

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.


2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.


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