Simple deaminations. V. Preparation and some properties of N-alkyl-N,N-disulfonimides

DeChristopher, Phillip J.; Adamek, John P.; Lyon, Gregory D.; Klein, S.A.; Baumgarten, Ronald J.

doi:10.1021/jo00938a017

Cited by 59 publications

(23 citation statements)

References 5 publications

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“…100 Heating or irradiation of a benzene solution of 9 did not lead to any C-O bond formation. The additional formation of NaN(SO 2 Ph) 2 was confirmed by NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 90%

Reactivity of platinum alkyne complexes towards N-fluorobenzenesulfonimide: formation of platinum compounds bearing a β-fluorovinyl ligand

et al. 2015

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The platinum(0) alkyne complexes [Pt(L)(η(2)-PhC[triple bond, length as m-dash]CPh)] 1-4 were synthesized by reactions of [Pt(cod)2] with diphenylacetylene and a phosphine ligand precursor (1: L = dcpe, 2: L = xantphos, 3: L = κ(2)-(P,N)-iPr2PC3H6NMe2, 4: L = κ(2)-(P,N)-iPr2PC2H4NMe2). Treatment of 1 or 4 with NFSI gave the complexes [Pt(F){N(SO2Ph)2}(dcpe)] (5) and [Pt(PhC[double bond, length as m-dash]CFPh){N(SO2Ph)2}{κ(2)-(P,N)-iPr2PC2H4NMe2}] (8), whereas the reactivity of 2 and 3 towards NFSI led to product mixtures. The compounds [Pt(F){N(SO2Ph)2}(xantphos)] (6a) as well as [Pt(PhC[double bond, length as m-dash]CFPh){N(SO2Ph)2}{κ(2)-(P,N)-iPr2PC2H4NMe2}] (7a) and [Pt(PhC[double bond, length as m-dash]CFPh)(F){κ(2)-(P,N)-iPr2PC2H4NMe2}] (7b) were clearly identified. Ligand exchange reactions at 8 resulted in the formation of the β-fluorovinyl platinum(ii) complexes [Pt(PhC[double bond, length as m-dash]CFPh){OC(O)CF3}{κ(2)-(P,N)-iPr2PC2H4NMe2}] (9), [Pt(PhC[double bond, length as m-dash]CFPh)(FHF){κ(2)-(P,N)-iPr2PC2H4NMe2}] (10) and [Pt(PhC[double bond, length as m-dash]CFPh)(F){κ(2)-(P,N)-iPr2PC2H4NMe2}] (11). Treatment of 8 with dihydrogen yielded the fluorinated olefin (Z)-(1-fluoroethene-1,2-diyl)dibenzene and [Pt{N(SO2Ph)2}(H){κ(2)-(P,N)-iPr2PC2H4NMe2}] (12).

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“…100 Heating or irradiation of a benzene solution of 9 did not lead to any C-O bond formation. The additional formation of NaN(SO 2 Ph) 2 was confirmed by NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 90%

Reactivity of platinum alkyne complexes towards N-fluorobenzenesulfonimide: formation of platinum compounds bearing a β-fluorovinyl ligand

et al. 2015

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“…In the case of the N-allyl-N-phenylsulfonylbenzamide derivatives, ortho-halogen substituents on the benzene ring of the benzoyl moiety increased the activity,7) whereas in the N-(2,3-epoxypropyl)-N-phenylsulfonylbenzamides, such substituents (5 and 8) were less active than the meta-substituted derivative (6). This difference in the structural requirements for high activity in these two types of compounds clearly indicates that the possibility of further activation by epoxidation of the allyl group is very low and thus, both types of compounds themselves are active forms.…”

Section: 7)mentioning

confidence: 98%

Herbicidal Activity ofN-(2,3-Epoxypropyl)benzenesulfonamide Derivatives

Yoneyama¹,

Ichizen²,

Konnai³

et al. 1985

Agricultural and Biological Chemistry

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“…3a-c, in diethyl ether or dioxane (for a review see [2]). This reaction initially forms a complex ammonium salt with a proposed formula of C 8 F 17 SO 2 NR − · NRH 3 + · NRH 3 F. The desired alkylated perfluorooctanesulfonamide 5a-c is subsequently isolated after thermal decomposition of this complex salt [8][9][10][11] or by treatment of the reaction mixture with hydrochloric or sulfuric acid [11][12][13]. Following these previous reports, we initially investigated the reaction of perfluorooctanesulfonyl fluoride (1) by using an excess of the respective alkyl amine, e.g.…”

Section: Synthesis Of N-alkyl and Nn-dialkyl Perfluoroalkanesulfonammentioning

confidence: 99%

“…1 H, 13 C and 19 F NMR spectra were recorded on a Bruker Avance-300 spectrometer. All NMR chemical shifts (δ) are reported in parts per million (ppm) and were determined relative to TMS for 1 H and 13 C NMR spectra and CFCl 3 for 19 F NMR spectra.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

Synthesis and structure of environmentally relevant perfluorinated sulfonamides

Lehmler

Rao

Nauduri

et al. 2007

Journal of Fluorine Chemistry

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Alkylated perfluorooctanesulfonamides are compounds of environmental concern. To make these compounds available for environmental and toxicological studies, a series of N-alkylated perfluorooctanesulfonamides and structurally related compounds were synthesized by reaction of the corresponding perfluoroalkanesulfonyl fluoride with a suitable primary or secondary amine. Perfluoroalkanesulfonamidoethanols were obtained from the N-alkyl perfluoroalkanesulfonamides either by direct alkylation with bromoethanol or alkylation with acetic acid 2-bromo-ethyl ester followed by hydrolysis of the acetate. N-Alkyl perfluorooctanesulfonamidoacetates were synthesized in an analogous way by alkylation of N-alkyl perfluoroalkanesulfonamides with a bromo acetic acid ester, followed by basic ester hydrolysis. Alternatively, N-alkyl perfluoroalkanesulfonamides can be alkylated with an appropriate alcohol using the Mitsunobu reaction. Perfluorooctanesulfonamide was synthesized from the perfluorooctanesulfonyl fluoride via the azide by reduction with Zn/HCl. All perfluorooctanesulfonamides contained linear as well as branched C 8 F 17 isomers, typically in a 20:1 to 30:1 ratio. The crystal structures of N-ethyl and N,N-diethyl perfluorooctanesulfonamide show that the S-N bond has considerable double bond character. This double bond character results in a significant rotational barrier around the S-N bond (ΔG ≠ = 62-71 kJ mol −1 ) and a preferred solid state and solution conformation in which the N-alkyl groups are oriented opposite to the perfluorooctyl group to minimize steric crowding around the S-N bond.

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Simple deaminations. V. Preparation and some properties of N-alkyl-N,N-disulfonimides

Cited by 59 publications

References 5 publications

Reactivity of platinum alkyne complexes towards N-fluorobenzenesulfonimide: formation of platinum compounds bearing a β-fluorovinyl ligand

Reactivity of platinum alkyne complexes towards N-fluorobenzenesulfonimide: formation of platinum compounds bearing a β-fluorovinyl ligand

Herbicidal Activity ofN-(2,3-Epoxypropyl)benzenesulfonamide Derivatives

Synthesis and structure of environmentally relevant perfluorinated sulfonamides

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