The synthesis of Tetracyclo[5,3,1,03,5,04,9]undecan-2-one and the acid-catalysed and reductive cleavages of the cyclopropyl ring

1975 ◽  
Vol 28 (10) ◽  
pp. 2255 ◽  
Author(s):  
DPG Hamon ◽  
GF Taylor
Keyword(s):  
Acetic Acid ◽  
Double Bond ◽  
Liquid Ammonia ◽  
Aqueous Acetic Acid ◽  
Bromide Ion ◽  
Independent Synthesis

Tetracyclo[5,3,1,03,5,04,9]undecan-2-one (2,4-dehydro-5-homoadamantanone) (3) was synthesized by copper-catalysed intramolecular insertion of a diazoketone into a double bond. Acid-catalysed opening of the cyclopropyl ring in aqueous acetic acid cleaved the C3-C4 bond to give a mixture of exo-7-hydroxytricyclo[4,3,1,13,8]undecan-4-one (13) and its acetate (12). Under the same conditions except for the presence of bromide ion, a mixture of (12), (13) and exo-7- bromotricyclo[4,3,1,13,8]-undecan-4-one (17) was obtained. Reduction of (17) with LiAlH4 gave homoadamantanol. Reduction of (3) with lithium in liquid ammonia gave cleavage of the C 3-C 5 bond to afford tricyclo[5,3,1,04,9]-undecan-2-one (4), the structure of which was confirmed by independent synthesis.

Novel Compound from Flowers of Moringa oleifera Active Against Multi- Drug Resistant Gram-negative Bacilli

2020 ◽  
Vol 20 (1) ◽  
pp. 69-75
Author(s):  
Santi M. Mandal ◽  
Subhanil Chakraborty ◽  
Santanu Sahoo ◽  
Smritikona Pyne ◽  
Samaresh Ghosh ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Moringa Oleifera ◽  
Aqueous Acetic Acid ◽  
Phytochemical Analysis ◽  
Hydroxyl Groups ◽  
Drug Resistant ◽  
Gram Negative ◽  
Isolated Compound ◽  
Conventional Antibiotics

Background: The need for suitable antibacterial agents effective against Multi-drug resistant Gram-negative bacteria is acknowledged globally. The present study was designed to evaluate the possible antibacterial potential of an extracted compound from edible flowers of Moringa oleifera. Methods: Five different solvents were used for preparing dried flower extracts. The most effective extract was subjected to fractionation and further isolation of the active compound with the highest antibacterial effect was obtained using TLC, Column Chromatography and reverse phase- HPLC. Approaches were made for characterization of the isolated compound using FTIR, NMR and Mass spectrometry. Antibacterial activity was evaluated according to the CLSI guidelines. Results: One fraction of aqueous acetic acid extract of M. oleifera flower was found highly effective and more potent than conventional antibiotics of different classes against Multi-drug resistant Gram-negative bacilli (MDR-GNB) when compared. The phytochemical analysis of the isolated compound revealed the presence of hydrogen-bonded amine and hydroxyl groups attributable to unsaturated amides. Conclusion: The present study provided data indicating a potential for use of the flowers extract of M. oleifera in the fight against infections caused by lethal MDR-GNB. Recommendations: Aqueous acetic acid flower extract of M. oleifera is effective, in-vitro, against Gram-negative bacilli. This finding may open a scope in pharmaceutics for the development of new classes of antibiotics.

Coordination state of cobalt(II) ions in solution and on a sulphonated organic polymer

1979 ◽  
Vol 44 (8) ◽  
pp. 2330-2337 ◽  
Author(s):  
Jindřiška Maternová ◽  
Anastas A. Andreev ◽  
Dimitrii M. Shopov ◽  
Karel Setínek
Keyword(s):  
Acetic Acid ◽  
Coordination Sphere ◽  
Glacial Acetic Acid ◽  
Organic Polymer ◽  
Octahedral Complex ◽  
Coordination State ◽  
Tetrahedral Symmetry ◽  
Liquid Acid ◽  
Homogeneous Phase ◽  
Bromide Ion

It was found spectroscopically that cobalt(II) acetate dissolved in glacial acetic acid forms the octahedral complex [Co(OAc)2(HOAc)4] which in the presence of bromide ions gives the octahedral [Co(OAc)Br(HOAc)4] and tetrahedral bromo(acetate)cobalt(II) complexes with the higher number of Br- ions. When attached to an organic polymer cobalt(II) ions are bonded in the form of octahedral [Co(H2O)6]2+ cations which form with acetic acid similar complexes as in homogeneous phase and are able to coordinate one bromide ion. Drying the copolymer possessing octahedral hexaaquocobalt(II) cations leads to tetrahedral aquocomplexes which are solvated by gaseous acetic acid and converted into the acetate complexes with the liquid acid. The latter contain the acid in the inner coordination sphere and have tetrahedral symmetry.

Synthesis and properties of 1,3-bis(4-nitrophenyl)-1-butene

1980 ◽  
Vol 45 (7) ◽  
pp. 2120-2124 ◽  
Author(s):  
Gabriel Čík ◽  
Anton Blažej ◽  
Kamil Antoš ◽  
Igor Hrušovský
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Double Bond ◽  
Fuming Nitric Acid

1,3-Bis(4-nitrophenyl)-1-butene was prepared by nitration of 1,3-diphenyl-1-butene (I) with fuming nitric acid in acetic acid. The double bond in I was protected by addition of bromine which was eliminated after the nitration. The UV, IR and 1H- spectra of the synthesized compounds are interpreted.

Reaction of 30-nor-18-lupene derivatives with bromine and peracids

1984 ◽  
Vol 49 (1) ◽  
pp. 141-149
Author(s):  
Eva Klinotová ◽  
Jiří Protiva ◽  
Jiří Klinot ◽  
Alois Vystrčil
Keyword(s):  
Acetic Acid ◽  
Double Bond

The reaction of diol I and diacetate IIwith one mole of bromine gives rise, depending on conditions, to isomeric dienes III-V and IX or to derivatives substituted in position 21 (VII, VIII). On reaction of diacetate II with two moles of bromine in acetic acid 21,22-disubstituted compounds XI and XII were obtained. Diene V is the intermediate in the formation of dienes IV and IX and derivatives XI and XII. Epoxidation of the 18(19)-double bond in compounds I and II takes place from the β-side and leads for epoxides XIV and XV.

Compatibility studies of chitosan/PVA blend in 2% aqueous acetic acid solution at 30°C

2010 ◽  
Vol 82 (2) ◽  
pp. 251-255 ◽  
Author(s):  
H.M.P. Naveen Kumar ◽  
M.N. Prabhakar ◽  
C. Venkata Prasad ◽  
K. Madhusudhan Rao ◽  
T.V. Ashok Kumar Reddy ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Acid Solution ◽  
Acetic Acid Solution ◽  
Aqueous Acetic Acid ◽  
Compatibility Studies ◽  
Aqueous Acetic Acid Solution

scholarly journals Perborate Oxidation of Substituted 5-Oxoacids in Aqueous Acetic Acid Medium: A Kinetic and Mechanistic Study

2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
S. Shree Devi ◽  
B. Muthukumaran ◽  
P. Krishnamoorthy
Keyword(s):  
Acetic Acid ◽  
Acid Medium ◽  
Reaction Rate ◽  
Reaction Medium ◽  
Activation Parameters ◽  
Reaction Rates ◽  
Mechanistic Study ◽  
Aqueous Acetic Acid ◽  
Sodium Perborate ◽  
Acetic Acid Medium

Kinetics and mechanism of oxidation of substituted 5-oxoacids by sodium perborate in aqueous acetic acid medium have been studied. The reaction exhibits first order both in [perborate] and [5-oxoacid] and second order in [H+]. Variation in ionic strength has no effect on the reaction rate, while the reaction rates are enhanced on lowering the dielectric constant of the reaction medium. Electron releasing substituents in the aromatic ring accelerate the reaction rate and electron withdrawing substituents retard the reaction. The order of reactivity among the studied 5-oxoacids is p-methoxy ≫ p-methyl > p-phenyl > –H > p-chloro > p-bromo > m-nitro. The oxidation is faster than H2O2 oxidation. The formation of H2BO3+ is the reactive species of perborate in the acid medium. Activation parameters have been evaluated using Arrhenius and Eyring’s plots. A mechanism consistent with the observed kinetic data has been proposed and discussed. Based on the mechanism a suitable rate law is derived.

scholarly journals Kinetics and mechanism of meso-tetraphenylporphyriniron(III) chloride (TPP) catalysed oxidation of indole by sodium perborate

2013 ◽  
Vol 15 (2) ◽  
pp. 107-111 ◽  
Author(s):  
D. Kungumathilagam ◽  
K. Karunakaran
Keyword(s):  
Acetic Acid ◽  
Catalytic Activity ◽  
Reaction System ◽  
Kinetic Scheme ◽  
Mechanistic Study ◽  
Radical Mechanism ◽  
Aqueous Acetic Acid ◽  
Sodium Perborate ◽  
Acetic Acid Medium ◽  
Catalysed Oxidation

Developing catalyst is very significant for biologically important reactions which yield products, used as drugs. Mechanistic study on meso-tetraphenylporphyriniron(III) chloride (TPP) catalysed oxidation of indole by sodium perborate in aqueous acetic acid medium have been carried out. The reaction follows a fractional order with respect to substrate and catalyst. The order with respect to oxidant was found to be one. Increase in the percentage of acetic acid and increase in the concentration of [H+] decreased the rate. The reaction fails to initiate polymerization, and a radical mechanism is ruled out. Activation and thermodynamic parameters have been computed. A suitable kinetic scheme based on these observations has been proposed. Significant catalytic activity is observed for the reaction system in the presence of TPP.

scholarly journals Catalytic valorization of hardwood for enhanced xylose-hydrolysate recovery and cellulose enzymatic efficiency via synergistic effect of Fe3+ and acetic acid

2019 ◽  
Vol 12 (1) ◽  
Author(s):  
Kaixuan Huang ◽  
Lalitendu Das ◽  
Jianming Guo ◽  
Yong Xu
Keyword(s):  
Acetic Acid ◽  
Synergistic Effect ◽  
Paper Industry ◽  
Enzymatic Saccharification ◽  
Value Added ◽  
Lewis Acid Site ◽  
Aqueous Acetic Acid ◽  
Xylan Degradation ◽  
Hydrolysis Process ◽  
Xylonic Acid

Abstract Background Poplars are considered suitable dedicated energy crops, with abundant cellulose and hemicellulose, and huge surplus biomass potential in China. Xylan, the major hemicellulosic component, contributes to the structural stability of wood and represents a tremendous quantity of biobased chemicals for fuel production. Monomeric xylose conversion to value-added chemicals such as furfural, xylitol, and xylonic acid could greatly improve the economics of pulp-paper industry and biorefinery. Acetic acid (HAc) is used as a friendly and recyclable selective catalyst amenable to xylan degradation and xylooligosaccharides production from lignocellulosic materials. However, HAc catalyst usually works much feebly at inert woods than agricultural straws. In this study, effects of different iron species in HAc media on poplar xylan degradation were systematically compared, and a preferable Fe3+-assisted HAc hydrolysis process was proposed for comparable xylose-hydrolysate recovery (XHR) and enzymatic saccharification of cellulose. Results In presence of 6.5% HAc with 0.17–0.25 wt% Fe3+, xylose yield ranged between 72.5 and 73.9%. Additionally, pretreatment was effective in poplar delignification, with a lignin yield falling between 38.6 and 42.5%. Under similar conditions, saccharification efficiency varied between 60.3 and 65.9%. Starting with 100 g poplar biomass, a total amount of 12.7–12.8 g of xylose and 18.8–22.8 g of glucose were harvested from liquid streams during the whole process of Fe3+-HAc hydrolysis coupled with enzymatic saccharification. Furthermore, the enhancement mechanism of Fe3+ coupled with HAc was investigated after proof-of-concept experiments. Beechwood xylan and xylose were treated under the same condition as poplar sawdust fractionation, giving understanding of the effect of catalysts on the hydrolysis pathway from wood xylan to xylose and furfural by Fe3+-HAc. Conclusions The Fe3+-assisted HAc hydrolysis process was demonstrated as an effective approach to the wood xylose and other monosaccharides production. Synergistic effect of Lewis acid site and aqueous acetic acid provided a promising strategy for catalytic valorization of poplar biomass.

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