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Wittig and Wittig-Horner reactions under phase transfer catalysis conditions

100%
Pascariu A., Ilia G., Bora A., Bora A., Iliescu S., Popa A., Dehelean G., Pacureanu L.
Open Chemistry
|
2003
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vol. 1
|
issue 4
491-534
EN
Wittig and Wittig-Horner reactions are favorite tools in preparative organic chemistry. These olefination methods enjoy widespread and recognition because of their simplicity, convenience, and effciency. Phase transfer catalysis (PTC) is a very important method in synthetic organic chemistry having many advantages over conventional, homogenous reaction procedures. In this paper, we attempt to summarize the aspects concerning Wittig and Wittig-Horner reactions that take place under phase transfer catalysis conditions.
2
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Comparison of the methods of the phase transfer catalysis and hydroperoxide in the epoxidation of 1,5,9-cyclododecatriene

88%
Lewandowski G.
Polish Journal of Chemical Technology
|
2007
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vol. 9
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issue 3
101-104
EN
The process of the epoxidation of cis, trans, trans-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) with the 30% aqueous hydrogen peroxide under the phase transfer conditions and with tert-butyl hydroperoxide under the homogeneous conditions was investigated. Onium salts such as Aliquat® 336, Arquad® 2HT, methyltrioctylammonium bromide and the Na2WO4/H3PO4 catalyst system are very active under the phase transfer catalysis (PTC) conditions for the selective epoxidation of cis, trans, trans-1,5,9-cyclododecatiene (PTC method). These catalytic systems were found to be as active and selective as the homogeneous phase system Mo(CO)6/TBHP (hydroperoxide method).
3
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Efficiency of selected phase transfer catalysts for the synthesis of 1,2-epoxy-5,9-cyclododecadiene in the presence of H2O2/H3PW12O40as catalytic system

88%
Lewandowski G.
Polish Journal of Chemical Technology
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2013
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vol. 15
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issue 3
96-99
EN
The results of the studies on the influence of the phase transfer catalyst on the epoxidation of (Z,E,E)-1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) in the H2O2/H3PW12O40 system by a method of phase transfer catalysis (PTC) were presented. The following quaternary ammonium salts were used as phase transfer catalysts: methyltributylammonium chloride, (cetyl)pyridinium bromide, methyltrioctylammonium chloride, (cetyl)pyridinium chloride, dimethyl[dioctadecyl(76%)+dihexadecyl(24%)] ammonium chloride, tetrabutylammonium hydrogensulfate, didodecyldimethylammonium bromide and methyltrioctylammonium bromide. Their catalytic activity was evaluated on the basis of the degree of CDT and hydrogen peroxide conversion and the selectivities of transformation to ECDD in relation to consumed CDT and hydrogen peroxide. The most effective PT catalysts were selected based on the obtained results. Among the onium salts under study, the epoxidation of CDT with hydrogen peroxide proceeds the most effectively in the presence of methyltrioctylammonium chloride (Aliquat® 336) and (cetyl)pyridinium chloride (CPC). The relatively good results of CDT epoxidation were also achieved in the presence of Arquad® 2HT and (cetyl)pyridinium bromide
4
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2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

63%
Gajdoš P., Pavlíková S., Bureš F., Krutošíková A.
Open Chemistry
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2005
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vol. 3
|
issue 2
311-325
EN
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.
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