Boron Trifluoride-promoted Reaction Research Articles

ChemInform Abstract: Boron Trifluoride-Promoted Reaction of Arenesulfinic Acids with Phthalaldehydic Acids: Enroute to 3-Arylsulfonylphthalides.

ChemInform Abstract: Boron Trifluoride-Promoted Reaction of Arenesulfinic Acids with Phthalaldehydic Acids: Enroute to 3-Arylsulfonylphthalides.

ChemInform Abstract: Boron Trifluoride Promoted Reaction of p-Nitrobenzenesulfenanilide with Alkynes. A Further Insight into the Reactivity of the Resulting Thiirenium Ion Intermediates.

ChemInform Abstract: Boron Trifluoride Promoted Reaction of p-Nitrobenzenesulfenanilide with Alkynes. A Further Insight into the Reactivity of the Resulting Thiirenium Ion Intermediates.

A New Synthetic Method for α-Oxo-β,γ-unsaturated Esters

Abstract α-Oxo-β,γ-unsaturated esters have been prepared in moderate to good yields via a two-step procedure consisting of the boron trifluoride-promoted reaction of 2-(trimethylsiloxy)acrylic esters with acetals, followed by treatment with silica gel in benzene under reflux.

Stereoselective synthesis of glycosides and anomeric azides of glucosamine

The β-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phasetransfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of β-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.

ChemInform Abstract: An Unusual Rearrangement in the Boron Trifluoride‐Promoted Reaction of Tetracyclo(6.3.0.04,11.05,9)undecane‐2,7‐dione Monoethylene Acetal with Ethyl Diazoacetate.

AbstractThe product (III) (space group P1 with Z=2) of the title reaction is composed of six fused five‐membered rings with three recognizable norbornane moieties.

Boron trifluoride-promoted reaction of 4′-nitrobenzenesulphenanilide with alkynes. Formal addition of benzenesulphenyl fluoride to carbon–carbon triple bonds

The BF3-promoted reaction of 4′-nitrobenzenesulphenanilide with simple alkyl- and aryl-alkynes at 80 °C in the presence of tetrabutylammonium tetrafluoroborate provides a one-pot synthetic route to β-fluorovinyl sulphides via a formal regioselective and trans-stereospecific addition of benzenesulphenyl fluoride towards carbon–carbon triple bonds.

Boron trifluoride-promoted reaction of 4′-nitrobenzenesulphenanilide and its N-methyl derivative with alkynes

4′-Nitrobenzenesulphenanilide and its N-methyl derivative react with alkynes in the presence of boron trifluoride–diethyl ether presumably affording thiirenium ion intermediates, which are trapped by acetonitrile to give eventually β-acetamidinovinyl sulphides.

Boron trifluoride-promoted reaction of benzenesulphenanilides with alkenes in acetonitrile and benzonitrile: amidino- and amido-sulphenylation of alkenes

Benzenesulphenanilides (1) react at room temperature with alkenes in acetonitrile or benzonitrile in the presence of boron trifluoride–diethyl ether to give amidino sulphides (5; R = Me, Ph) in fair to good yields together with varying amounts of amido sulphides (7; R = Me, Ph) and arylamino sulphides (4), whereas at 100 °C and in the presence of water 4′-nitrobenzenesulphenanilide affords amido sulphides (7; R = Me, Ph) as the main products. With cyclohexene a high selectivity for trans-addition is observed. With terminal alkenes the terminal sulphides are produced with high regioselectivity. The findings are consistent with a mechanism involving intermediacy of episulphonium ions (3) which result from alkene attack at the sulphur atom of an anllide–BF3 complex.

Boron trifluoride promoted reaction of benzenesulphenanilides with alkenes

The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides. The benzenesulphenanilides (1) investigated generally afford arylamino-sulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (le and f), which largely lead to decomposition products under comparable conditions. In all cases examined, the addition proceeds with trans -stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides. The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.

ChemInform Abstract: BORON TRIFLUORIDE‐PROMOTED REACTION OF BENZENESULFENANILIDES WITH ALKENES ‐ ARYLAMINOSULFENYLATION OF ALKENES

Chemischer InformationsdienstVolume 15, Issue 35 Isocyclic Compounds ChemInform Abstract: BORON TRIFLUORIDE-PROMOTED REACTION OF BENZENESULFENANILIDES WITH ALKENES - ARYLAMINOSULFENYLATION OF ALKENES L. BENATI, L. BENATISearch for more papers by this authorP. C. MONTEVECCHI, P. C. MONTEVECCHISearch for more papers by this authorP. SPAGNOLO, P. SPAGNOLOSearch for more papers by this author L. BENATI, L. BENATISearch for more papers by this authorP. C. MONTEVECCHI, P. C. MONTEVECCHISearch for more papers by this authorP. SPAGNOLO, P. SPAGNOLOSearch for more papers by this author First published: August 28, 1984 https://doi.org/10.1002/chin.198435188Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume15, Issue35August 28, 1984 RelatedInformation