Cesium fluoride promoted formation of n-chloro and n-bromo amines and imines

DesMarteau, Darryl D.; O'Brien, Brian A.; Mir, Q.C.; Zheng, Yang

doi:10.1016/s0022-1139(00)85501-3

Cited by 5 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The use of fluoride ion (F − ) as a base or catalyst in organic syntheses has gained significant popularity for display a high tolerance for functional groups . We have linked several other investigators in reporting on CsF‐catalyzed conversions of various carbonyl compounds with a variety of functional groups like benzamides, disulfides, ethers, amines, and fluoromethanimine . CsF as well famous for the desilylative elimination, palladium, coupling, Julia‐Kocienski olefination, Aza‐Michael, and Claisen rearrangement .…”

Section: Introductionmentioning

confidence: 99%

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

Wagh

Padvi²,

Mahulikar

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

Wagh

Padvi²,

Mahulikar

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Synthese und Eigenschaften von N , N ‐Dihalogen‐1,1‐difluoraminen RCF ₂ NXX′

1985

View full text Add to dashboard Cite

Aus der Umsetzung der Nitrile X-CN (la-4a, X = CI, CF3, CC13, CH3) mit Chlor und Brom lassen sich die N,N-Dihalogen-1,l-difluoramine R-CF2-NX2 (R = F, CF?, CC13, CH3; l d -4 d X = C1, le-4e: X = Br) in hohen Ausbeuten darstellen. Synthesewege zu den nicht in reiner Form isolierten Bromchloraminen RCF2NBrC1 (lg-4g) werden aufgezeigt. Im Falle der Ethylverbindungen lassen sich durch Wahl der Stochiometrie die Imine RCF=NX (2b-4b: X = C1; 2c-4c: X = Br) erzeugen. Sowohl Thermolyse als auch Photolyse der Amine fiihrt zu den Diazenen (R-CF,-N=),(lf-40. Synthesis and Properties of N,N-Dihalo-1,l-difluoroamines R -CF2 -NXX'The nitriles X-CN (la-4a, X = C1, CF3, CCl3, CH3) react with chlorine and bromine to form N,N-dihalo-1,l-difluoroamines R-CFz-NXz (R = F, CF3, CC13, CHI; ld-4d: X = CI; le-4e: X = Br) in high yields. Routes are shown for the synthesis of bromochloroamines RCF,NBrCl (lg-4g), which could not be isolated in pure state. For the ethyl derivatives the imines R-CF=NX (2b-4b X = C1; 2c-4c: X = Br) were obtained in good yields by using the appropriate stoichiometry. Both thermolysis and photolysis of the amines give the diazenes (R-CF2-N=)* (If-40.N,N-Dihalogenarnine und N-Halogenimine (Halogen = Chlor oder Brom) besitzen aufgrund der Labilitat der Stickstoff-Halogenbindung grol3e Bedeutung fur die praparative Chemie". Einen Uberblick uber Darstellung und Eigenschaften der bisher bekannten Perhalogenalkyl-N-Halogenverbindungen gibt ein kiirzlich erschienener Gmelin-Band'). RHdCN + C1F +

show abstract

Über die Chlor‐ und Brom‐Fluorierung acyclischer und cyclischer CN‐Mehrfachbindungssysteme

Geisel

Mews

1986

Chem. Ber.

View full text Add to dashboard Cite

Durch Urnsetzung der Nitrile R-C=N [R = NSF2 (l), NSOF, (911 mit C12 bzw. Br2 in Gegenwart von HgF2 werden die entsprechenden N,N-Dihalogen-1,l-difluormethanamine R-CF2-NXX' (R = NSF2, X = X' = C1, Br; X = C1, X' = Br (5b, 6, 7); R = NSOF2, X = X' = CI, Br; X = C1, X' = Br (14, 15, 16)] dargestellt. Aus ihnen bilden sich durch Photolyse die Diazene (R-CF,-N=), [R = NSF2, NSOF2 (8, 1711. N-(Difluor-h4sulfanyliden)-2-(halogenimino)ethanamin-Derivate FzSN -CF2 -CF = NX [X = C1, Br (20, 21)] bzw. N-(Difluor-h4-sulfanyliden)-N',N'-dihalogen-l ,2-ethandiamine F2SN -CF2 -CF2-NXX' [X = X' = C1, Br; X = C1, X = Br (22-24)] entstehen auf gleichem Wege durch Spaltung von 3,CDifluor-t ,2,5-thiadiazol (18). Das Diazen (F2SN-CF2-CF2-N=), (28)] ist ebenfalls als Folgeprodukt erhaltlich. In (NCF)3 (29) bleibt unter den Bedingungen dieser Chlorfluorierung das Ringgeriist erhalten, und (CINCF2)3 (30) wird in hohen Ausbeuten isoliert. Chloro-and Bromo-Fluorination of Acyclic and Cyclic CN Multiple Bond Systems From nitriles R-C = N [R = NSF2 (I), NSOF2 (9)] and C12 or Br2 in the presence of HgF2 N,N-dihalo-1,l-difluoromethanamines R-CF2-NXX [R = NSF2, X = X' = C1, Br; X = CI, X' = Br (5b, 6, 7); R = NSOF2, X = X' = C1, Br; X = C1, X' = Br (14, 15, 16)] are obtained. These on photolysis give diazenes (R-CF2-N=)2 [R = NSF2, NSOFz (8, 1711. N-(Difluoro-h4-sulfanylidene)-2-( ha1oimino)ethanamine derivatives F2SN -CF2 -CF = NX [X = C1, Br (20, 2111 and N-(difluoro-h4-sulfanylidene)-N"'-dihalo-1,2-ethanediamines F2SN-CF2-CF2-NXX' [X = X' =C1, Br; X = C1, X' = Br (22-24)], respectively, are prepared on the same route by cleavage of 3,4-difluoro-1,2,5-thiadiazole (18).The diazene (F2SN-CF2-CF2 -N=)2 (28) is formed by subsequent photolysis. Under the conditions of this chloro-fluorination in (NCF)3 (29) the cyclic structure is stable, (CINCF2)3 (30) is isolated in high yield. N,N-Dihalogenfluoralkanamine sind in den letzten Jahren Gegenstand intensiver Forschung gewesen1-15). Die praparativen Moglichkeiten, die sich aus der Labilitat der Stickstoff-Halogen-Bindung ergeben (Halogen = C1 bzw. Br), sind vielfiltig16-20'. Besonders groBe Bedeutung als Iminierungsreagens werden die N,N-Dibromamine8 -'

show abstract

Cesium fluoride promoted formation of n-chloro and n-bromo amines and imines

Cited by 5 publications

References 0 publications

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

Synthese und Eigenschaften von N , N ‐Dihalogen‐1,1‐difluoraminen RCF ₂ NXX′

Über die Chlor‐ und Brom‐Fluorierung acyclischer und cyclischer CN‐Mehrfachbindungssysteme

Contact Info

Product

Resources

About

Cesium fluoride promoted formation of n-chloro and n-bromo amines and imines

Cited by 5 publications

References 0 publications

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

Synthese und Eigenschaften von N , N ‐Dihalogen‐1,1‐difluoraminen RCF 2 NXX′

Über die Chlor‐ und Brom‐Fluorierung acyclischer und cyclischer CN‐Mehrfachbindungssysteme

Contact Info

Product

Resources

About

Synthese und Eigenschaften von N , N ‐Dihalogen‐1,1‐difluoraminen RCF ₂ NXX′