sym-Difluorotetrachloroacetone as a Source of Chlorofluorocarbene

Farah, Basil S.; Horensky, S.

doi:10.1021/jo01044a538

Cited by 22 publications

(7 citation statements)

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“…Fluorochlorocarbene was generated by the action of potassium /-butoxide on spm-tetrachlorodifluoroacetone according to the procedure of Farah and Horensky. 19 The physical and chemical properties are in accord with the cyclopropane structure and also with the recent report of Weyerstahl, et al,w who prepared the compound by another method.…”

Section: Synthesissupporting

confidence: 80%

Dihedral angle and bond angle dependence of vicinal proton-fluorine spin-spin coupling

Williamson¹,

Hsu²,

Hall³

et al. 1968

J. Am. Chem. Soc.

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Section: Synthesissupporting

confidence: 80%

Dihedral angle and bond angle dependence of vicinal proton-fluorine spin-spin coupling

Williamson¹,

Hsu²,

Hall³

et al. 1968

J. Am. Chem. Soc.

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“…The Pyrolysis of Trichloropropionitrile and Dichloroacrylonitrile.•-The pyrolysis was carried out in the same manner as described in the previous paper.la The starting materials were introduced into the reaction tube by the leak method. The reaction conditions and the compositions CH2=CCN ->-HC=CCN (14) '^CH2=CC1CN standable that cyanoacetylene is inevitably produced in a small amount even from pure starting materials, though this does not exclude some other possibilities, 1.1 e.g., wall effect, etc., which may lead to the formation of cyanoacetylene directly from ,/3-dichloroacrylonitrile.…”

Section: Resultsmentioning

confidence: 99%

“…CC1=CCN + H• (ID than a simple elimination mechanism, and that the acrylonitrile is acting as a scavenger of the chlorine atom, which plays an important role in the reaction (eq [12][13][14]. If this is the case, then it is also under-Synthesis of Chlorocyanoacetylene.…”

Section: Resultsmentioning

confidence: 99%

Nitriles. III. Synthesis of chlorocyanoacetylene and cyanoacetylene, and a novel malononitrile synthesis from chlorocyanoacetylene

Hashimoto¹,

Matsumura²,

Saraie³

et al. 1970

J. Org. Chem.

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Pyrolysis of trichloropropionitrile and dichloropropionitrile at 900-1000°under reduced pressure provided a novel synthesis of chlorocyanoacetylene (ca. 80%) and cyanoacetylene (40-60%). Chlorocyanoacetylene reacted with ammonia to give malononitrile in high yields.Cyanoacetylene is a compound of considerable interest, because it has two conjugated triple bonds in the molecule and, perhaps, will find wide application in the synthesis of a variety of heterocyclic compounds. It may also be useful as a monomer in the chemistry of polymers. Although cyanoacetylene has been known for many years, its chemical properties remain uninvestigated, largely owing to lack of a convenient synthesis. The most orthodox method for its synthesis has been recorded by Moureu,1 2 and involves the dehydration of propiolamide with phosphorus pentoxide. Since propiolamide has to be prepared from acetylene by a series of reactions including carbonylation, esterification, and amidation, this approach is far from being practical. Several workers3 thereafter somewhat improved Moureu's method but could not alter its lengthy nature.Recently, several patents claim that cyanoacetylene can be prepared by the dehydration of propargylaldehyde oxime4 or by some gas-phase reactions of acetylene5 or acetonitrile6 with hydrogen cyanide at high temperatures.Chlorocyanoacetylene was first prepared by Kloster-Jensen7 by the reaction of chlorine with lithium cyanoacetylide and its melting point (42-42.5°) and ir and uv spectral data were recorded by the same author.Recently, Bjorvatten8 reported the X-ray crystallographic study of chlorocyanoacetylene with the sample supplied by Kloster-Jensen. However, for lack of a (1) (a) Paper II: N.

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“…Zur in situ-Erzeugung von Dihalocarbenen eignen sich verschiedene Methoden [12][13][14][15][16][17][18]. Eine Möglich-keit besteht in der Eliminierung von Halogenwasserstoff aus Haloform durch starke Basen [14,18].…”

Section: Ergebnisse Und Diskussionunclassified

“…Eine Möglich-keit besteht in der Eliminierung von Halogenwasserstoff aus Haloform durch starke Basen [14,18]. Da bei Umsetzungen derartig gewonnener Carbene mit Carbonylmetall-Verbindungen Basenreaktionen [19,20] eintreten können, wurde die für basenempfindliche organische Substrate anwendbare Phasentransfer-Katalyse [12,13] gewählt.…”

Section: Ergebnisse Und Diskussionunclassified

Darstellung und Eigenschaften von und Reaktionen mit metallhaltigen Heterocyclen, XLVII [1]. Einschiebungsreaktionen von phasentransferkatalytisch in situ erzeugten Dihalocarbenen in P-haltige Manganacycloalkane – Struktur und chemisches Verhalten der Reaktionsprodukte / Preparation and Properties of and Reactions with Metal-Containing Heterocycles, XLVII [1]. Insertion Reactions of Phase-Transfer-Catalytically in situ Generated Dihalocarbenes into P-Containing Manganacycloalkanes – Structure and Chemical

Lindner

Zinsser

Mayer

et al. 1985

Zeitschrift Für Naturforschung B

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Abstract The phase-transfer-catalytically in situ generated dihalocarbenes CCl2 and CBr2 are inserted into a β-C-H bond of the five-and six-membered phosphamanganacycloalkanes (OC)4[xxx] (1a, b) [n = 1(a), 2(b)] to give the functionalized metallacycles (OC)4[xxx](2a, a′, b, b′) [X = Cl: n = 1(a), 2(b); X = Br: n = 1(a′), 2(b′)]. 2b crystallizes in the orthorhombic space group Pbca with Z = 8 and has a distorted chair conformation with equatorial position of the CHCl2 group. The envelope conformation of 2a in solution was elucidated by means of 1H and 13C{1H} NMR spectroscopic investigations.

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sym-Difluorotetrachloroacetone as a Source of Chlorofluorocarbene

Cited by 22 publications

References 1 publication

Dihedral angle and bond angle dependence of vicinal proton-fluorine spin-spin coupling

Dihedral angle and bond angle dependence of vicinal proton-fluorine spin-spin coupling

Nitriles. III. Synthesis of chlorocyanoacetylene and cyanoacetylene, and a novel malononitrile synthesis from chlorocyanoacetylene

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