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Showing papers on "Boron trifluoride published in 1989"


Journal ArticleDOI
TL;DR: In this article, treatment of methyl 5-acetamido with thiophenol, phenylmethanethiol, and ethanethylamine in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3−5.

175 citations



Journal ArticleDOI
TL;DR: In this paper, an aldehyde and a 1,3-diene with N-sulfinyl-p-toluenesulfonamide/boron trifluoride etherate leads to products of an imino Diels-Alder reaction via an N-Sulfonyl imine produced in situ.

62 citations



Journal ArticleDOI
TL;DR: The complete set of the eight theoretically possible stereoisomeric 3,6,7-trihydroxy-5 beta-cholanic acids, four of which are new, related to hyocholic and muricholic acids were prepared from chenodeoxycholic acid.

46 citations


Journal ArticleDOI
TL;DR: MOPMO (modified Pfitzner-Moffatt conditions) as discussed by the authors combines a conjuguee de tributylstannyllithium and a reduction or an alkylation.
Abstract: Methode de fragmentation utilisant la combinaison MOPMO (modified Pfitzner-Moffatt conditions). La fragmentation, combinee a une addition conjuguee de tributylstannyllithium et une reduction ou une alkylation est un procede efficace d'ouverture reductrice et alkylante du cycle de cetones cycliques vinyliques. Les produits sont des composes carbonyles insatures d'une stereochimie determinee

32 citations


Journal ArticleDOI
TL;DR: Boron trifluoride etherate catalyzed the formal [2+2]cycloaddition of 2,3- O -isopropylidene derivatives of with enol ethers, vinyl sulfide, and disubstituted terminal olefins to afford chiral oxetanes as mentioned in this paper.

28 citations


Journal ArticleDOI
TL;DR: In this paper, the boron trifluoride promoted condensation of (Z )- anti-4-hydroxy-1-alkenyl carbamates and aldehydes yields the title compounds with high twofold diastereofacial selectivity.

27 citations


Journal ArticleDOI
TL;DR: Hypervalent iodine oxidation of 2-(trimethylsilyloxy)furan with iodosobenzene:boron trifluoride etherate in the presence of various nucleophiles yields 5-substituted-2(5H)-furanones as mentioned in this paper.

25 citations


Patent
12 Oct 1989
TL;DR: In this article, a process for the manufacture of an olefin oligomer is described, comprising the steps of polymerizing a monomer in the presence of boron trifluoride and a borsil alcohol complex as catalysts, to prepare a first oligomerization product, and then carrying out one of following steps (e.g., removing borsilon trifluride from the above first product by placing the product under a reduced pressure, blowing an inert gas into the product, or heating the product at a relatively low temperature, to
Abstract: A process for the manufacture of an olefin oligomer, comprising the steps of polymerizing an olefin monomer in the presence of boron trifluoride and a boron trifluoride-alcohol complex as catalysts, to prepare a first oligomerization product, and then carrying out one of following steps (a) to (c): (a) removing boron trifluoride from the above first product by (i) placing the product under a reduced pressure, (ii) blowing an inert gas into the product, or (iii) heating the product at a relatively low temperature, to thereby prepare a second oligomerization product, and then subjecting the second product to a precipitation treatment to separate the boron trifluoride-alcohol complex therefrom, (b) heating the above first product at a relatively elevated temperature to recover boron trifluoride, or (c) centrifuging the above first product to recover the boron trifluoride-alcohol complex. These steps allow the catalysts to be recovered while maintaining the activity thereof at a desired level.

22 citations


Journal ArticleDOI
TL;DR: Alkenyl aluminate reagents, obtained by hydroalumination of terminal alkynes followed by ate complexation with Meli, react readily with poorly reactive cyclic ethers such as cyclohexene oxide and oxetane, in the presence of BF3·Et2O.

Journal ArticleDOI
TL;DR: The total synthesis of silychristin, an anti-hepatotoxic flavonolignan, was described in this paper, where the key intermediate, the transdihydrobenzofuran (15) was synthesized as follows.
Abstract: The total synthesis of silychristin, an antihepatotoxic flavonolignan, is described. The key intermediate, the transdihydrobenzofuran (15) was synthesized as follows. Treatment of the chalcone epoxide (9) with boron trifluoride etherate and subsequent reduction with sodium borohydride gave exclusively the erythro-1, 2-diaryl-1, 3-propanediol (10). Hydrogenolysis of 10 with hydrogen over a palladium catalyst followed by cyclization of the debenzylation product (13) with boron trifluoride etherate in acetic acid afforded 15 as a single product.

Journal ArticleDOI
TL;DR: In the presence of boron trifluoride etherate, the ω-silyloxyallyltrimethylsilanes Me3SiO(CH2)nCH(CHCH 2)SiMe3 (n = 2, 3) regiospecifically react with aliphatic or aromatic aldehydes but less readily with alophatic ketones, to give unsaturated oxygen-containing heterocycles, such as 2-alkyl-2,3,6,7-tetrahydroox

Journal ArticleDOI
TL;DR: In the presence of boron trifluoride etherate in acetonitrile, Penta-O-benzoyl-alpha-D-glucopyranose was used to give 3.5% and 2.3% yields, respectively as mentioned in this paper.

Journal ArticleDOI
TL;DR: In this article, complete cleavage of boron tris-trifluoromethanesulfonate(triflate) and trisplastic compounds was studied at 200°C and a mechanism for the cleavage based on formation of the identified compounds is suggested.

Patent
17 Nov 1989
TL;DR: In this article, a process for recovering boron trifluoride from an impure gaseous borsic acid residue containing sulfur dioxide as an impurity was proposed.
Abstract: The present invention provides a process for recovering boron trifluoride from an impure gaseous boron trifluoride residue. The process comprises: (a) feeding an impure gaseous boron trifluoride residue containing sulfur dioxide as an impurity into a mixture of boric and sulfuric acids wherein the acid mixture absorbs boron trifluoride from the impure boron trifluoride residue and slightly absorbs or does not absorb sulfur dioxide from the impure gaseous boron trifluoride residue; and (b) removing the unabsorbed sulfur dioxide from the acid mixture. The present invention also provides a boron trifluoride preparation and purification process. The process comprises the steps of (a) reacting boric acid and fluorosulfuric acid in sulfuric acid to form a product; (b) distilling the product from step (a) to yield pure boron trifluoride and impure gaseous boron trifluoride; (c) feeding the impure gaseous boron trifluoride residue containing sulfur dioxide as an impurity into a mixture of boric and sulfuric acids wherein the acid mixture absorbs boron trifluoride from the impure gaseous boron trifluoride residue and only slightly absorbs sulfur dioxide from the impure gaseous boron trifluoride residue; and (d) removing the unabsorbed sulfur dioxide from the acid mixture. The recovered boron trifluoride may be used as a catalyst.

Journal ArticleDOI
TL;DR: In this paper, di-and poly-saccharides containing arabinosyl and xylosyl residues have been methylated and then subjected to reductive-cleavage with triethylsilane in the presence of either trimethylsilyl trifluoromethanesulfonate or boron triffluoride etherate and trimethyl silyl methane.

Journal ArticleDOI
TL;DR: In the presence of boron trifluoride, 2-isoxazolines undergo the addition of organolithiums to afford N-unsubstituted isoxazolidines in moderate to good yields.
Abstract: In the presence of boron trifluoride, 2-isoxazolines undergo the addition of organolithiums to afford N-unsubstituted isoxazolidines in moderate to good yields.

Journal ArticleDOI
TL;DR: Ketals react with 1,2bis(trimethylsiloxy)cyclopentene in the presence of a large excess of boron trifluoride etherate to provide 2,2-disubstituted 1,3-cyclohexanediones in very good yields as discussed by the authors.


Journal ArticleDOI
TL;DR: Etude du mecanisme de reaction ion-molecule en fonction de la temperature and de la pression is presented in this article, where the temperature and the pressure are taken into account.
Abstract: Etude du mecanisme de reaction ion-molecule en fonction de la temperature et de la pression

Journal ArticleDOI
TL;DR: The results of radiotracer experiments employing 18F and 35S or 14C are consistent with the occurrence of weakly adsorbed SF4 or F2CO at the surface of activated CsF in addition to permanently retained species SF5 and F3CO as discussed by the authors.
Abstract: Activation of CsF by thermal decomposition of its 1 : 1 adducts with hexafluoroacetone or carbonyl fluoride results in significantly greater activity with respect to its reactions with AsF5, BF3, and SF4 under heterogeneous conditions at room temperature, and enables reactions involving carbonyl fluoride and carbon dioxide to be studied. The results of radiotracer experiments employing 18F and 35S or 14C are consistent with the occurrence of weakly adsorbed SF4 or F2CO at the surface of activated CsF in addition to permanently retained species SF5– and F3CO–. Carbon dioxide interacts weakly with activated CsF. Room-temperature 18F exchange occurs between 18F-labelled F2CO and activated CsF. It is not observable in the other systems but does occur at 373 K. It is suggested that the CsF activation process results in a pore structure for the solid and that this is responsible for its increased reactivity.

Journal ArticleDOI
TL;DR: In this paper, treatment of methyl 5-acetamido with thiophenol, phenylmethanethiol, and ethanethylamine in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3−5.
Abstract: Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-d-glycero-d-galacto-2-nonulopyranosonate (1) severally with thiophenol, phenylmethanethiol, and ethanethiol in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3–5. Treatment of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-d-glycero- d-galacto-2-nonulopyranosyl chloride)onate (2) severally with thiophenol in the presence of N,N-di-isopropylethylamine, O-ethyl S-potassium dithiocarbonate, and O-ethyl S-potassium thiocarbonate gave the corresponding 2-thio-α-glycosides 7, 10, and 11, of which 10 was converted into the ethyl 2-thio-α-glycoside 9 on heating with N,N-dimethylformamide-sodium iodide. The phenyl 2-thioglycosides 3 and 7 were converted into the corresponding sulfones.

Patent
11 Apr 1989
TL;DR: In this article, a method for the polymerization of olefins with a prevailing content of 1-butene and cis-and trans-2-butenes in the mixture of hydrocarbons known as rafinate II, which is derived from the C₄-fractions after separation of 1,3-butadiene and isobutylene, was presented.
Abstract: The method consists in the polymerization of olefins with a prevailing content of 1-butene and cis- and trans-2-butenes in the mixture of hydrocarbons known as rafinate II, which is derived from the C₄-fractions after separation of 1,3-butadiene and isobutylene, under initiation with boron trifluoride (BF₃) or alkylaluminium chlorides with the general formulae R₂AlCl and RAlCl₂ (in which each R represents a C₁ to C₆-alkyl group) in the presence of hydrogen chloride (HCl), hydrogen fluoride (HF), or organic compounds with a reactive chlorine or fluorine bonded to a tertiary-, benzyl- or allyl-carbon atom, as coinitiators. The method according to the solution may be carried out in such a way, that rafinate II derived from the production of methyl tert-butyl ether or from the selective polymerization of isobutylene, in which 1-butene present in a concentration at least 20% is polymerized together with cis- and trans-2-butenes present in a concentration of at least 15%, at a temperature of +100°C to -70°C, to form to oily products with molar mass M n = 300 to 1200. Preferably the mixture derived as rafinate II from the production of methyl tert-butyl ether is first freed of methanol to the content lower than 300p ppm.

Journal ArticleDOI
TL;DR: In this paper, a pericyclized naphthalene system has been prepared in four steps from 1,8-naphthalenedicarboxylic anhydride in an overall yield of 35-78% using boron trifluoride etherate as a catalyst.
Abstract: The titled new pericyclized naphthalene system has been prepared in four steps from 1,8-naphthalenedicarboxylic anhydride in an overall yield of 35–78% The key step in the synthesis employed a dithioacetal-cyclization reaction of 1,8-bis(mercaptomethyl)naphthalene with carbonyl compounds using boron trifluoride etherate as a catalyst

Journal ArticleDOI
TL;DR: In this paper, the ring-opening polymerization of 2-phenyl aziridine was studied with several catalyst systems: boron trifluoride etherate, chlorhydric acid, perchloric acid, dimethyl sulfate and methyl triflate.
Abstract: The ring-opening polymerization of 2-phenyl aziridine was studied with several catalyst systems: boron trifluoride etherate, chlorhydric acid, perchloric acid, dimethyl sulfate and methyl triflate. The corresponding polyamine was obtained as a pale yellow solid with a number average molecular weight around 2,000–3,000. A kinetic study is discussed in the case of perchloric acid and methyl triflate.

Patent
15 Mar 1989
TL;DR: In this paper, the problem of obtaining a copolymer comprising oxyalkylene units which is highly deactivated and exhibits a good color tone by bulk-polymerization of a mixture of trioxane with a cyclic ether in the presence of a polymerization catalyst based on boron trifluoride and subsequently deactivating the catalyst with a nitrogen compound, such as an amine and the like, having a specific chemical structure.
Abstract: PROBLEM TO BE SOLVED: To obtain a copolymer comprising oxyalkylene units which is highly deactivated and exhibits a good color tone by bulk-polymerization of a mixture of trioxane with a cyclic ether in the presence of a polymerization catalyst based on boron trifluoride and subsequently deactivating the catalyst with a nitrogen compound, such as an amine and the like, having a specific chemical structure: SOLUTION: As cyclic ethers to be copolymerized with trioxane, there can be mentioned ethylene oxide, dioxolane, phenyl glycidyl ether and the like. These compounds are co-polymerized in an amount of 0.1-10 mole %, preferably 0.2-5 mole %, based on trioxane. As the polymerization catalyst is employed boron trifluoride, boron trifluoride hydrate or a coordination compound of an organic compound having O or S atom with boron trifluoride as an organic solvent solution. The nitrogen compound for the deactivation of the catalyst after the bulk polymerization is represented by the formula (wherein R are each H or 1-5C alkyl; and R is 1-10C alkylene) and is employed in an amount such that the number of the boron atoms in the polymerization catalyst is equal to or more than the number of nitrogen atoms therein. After the deactivation of the catalyst, the polymer is heated to 100-270 deg.C to give the product.


Journal ArticleDOI
TL;DR: In this paper, the biphenyl-2-carboxaldehyde has been found to undergo facile cyclization to the 9-ethylthiofluorenes (9EFL) with boron trifluoride etherate.

Journal ArticleDOI
TL;DR: In this article, it was shown that 4′-Nitrobenzenesulphenanilide reacts at room temperature with simple alkyl- and aryl-alkynes in acetic acid in the presence of boron trifluoride-diethyl ether to afford products of acetoxysulphenylation in moderate to good yields.
Abstract: 4′-Nitrobenzenesulphenanilide reacts at room temperature with simple alkyl- and aryl-alkynes in acetic acid in the presence of boron trifluoride–diethyl ether to afford products of acetoxysulphenylation in moderate to good yields. The addition products are generally produced with trans-stereospecificity and in a regioselective fashion (Markovnikov orientation). The findings are consistent with a mechanism involving intermediary of thiirenium ions which would result from alkyne attack at the sulphur atom of the anilide complexed with boron trifluoride.