Acetylation and Formylation of 3-Ferrocenylpyrroles

1999 ◽  
Vol 64 (1) ◽  
pp. 99-106
Author(s):  
Battsengel Gotov ◽  
Štefan Toma ◽  
Eva Solčániová
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aluminum Chloride ◽  
Acetyl Chloride ◽  
Trifluoroacetic Anhydride ◽  
Acid Mixture ◽  
Chloride Method

Acetylations of 3-ferrocenyl-1-methylpyrrole as well as 3-cyano-4-ferrocenylpyrrole and 3-cyano-4-ferrocenyl-1-methylpyrrole were performed. The course of the acylation is highly dependent on the acylation agent, that is acetyl chloride/aluminum chloride (method A), trifluoroacetic anhydride-acetic acid mixture (method B) or acetic anhydride/Sc(OTf)3 (method C). Method A gives the acetylation on ferrocene moiety, method B affords the trifluoroacetylation on pyrrole moiety and method C affords pyrrole moiety acetylation. Vielsmeier-Haack formylation gives the products of substitution on pyrrole moiety.

Hot-Tube Reactions of Dehydroabietic Acid with Ketene-Producing Reagents. Pyrolysis of the Acid Chloride and Symmetrical and Mixed Anhydride Derivatives of Dehydroabietic Acid

1973 ◽  
Vol 51 (19) ◽  
pp. 3236-3241 ◽  
Author(s):  
Ray F. Severson ◽  
Walter H. Schuller
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Acid Chloride ◽  
Acetyl Chloride ◽  
Dehydroabietic Acid ◽  
Mixed Anhydride ◽  
Temperature Range ◽  
Acid Isomerization ◽  
Derivatives Of ◽  
Isopropenyl Acetate

Dehydroabietic acid (1a) was reacted with diketene, acetic acid, acetic anhydride, isopropenyl acetate, acetyl chloride, and acetone on Vycor rod at 450 °C in a hot tube. Dehydroabietic anhydride (1b) and acetyl dehydroabietate (1c) were pyrolyzed at 450 °C and dehydroabietyl chloride (1d) was pyrolyzed over a temperature range of 290–500 °C. The major olefin products resulting from decarboxylation of the various derivatives were 19-norabieta-4,8,11,13-tetraene (2), 19-norabieta-4(18),8,11,13-tetraene (3), 19-norabieta-3,8,11,13-tetraene (4), and cis-1,10a-dimethyl-7-isopropyl-1,2,3,9,10,10a-hexahydrophenanthrene (5). High conversions to these compounds were obtained. In the presence of the ketene-producing reagents the olefins were oxidized to yield substantial amounts of retene (6), compounds 2 and 5 being the most readily dehydrogenated. The acid isomerization of 2, 3, 4, and 5 was studied using p-toluenesulfonic acid in toluene at 110 °C.

Color Reactions of Rubber and Gutta-Percha

1929 ◽  
Vol 2 (2) ◽  
pp. 193-196
Author(s):  
F. Kirchhof
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Zinc Chloride ◽  
Trichloroacetic Acid ◽  
Acetyl Chloride ◽  
Oxidation Products ◽  
Arsenic Trichloride ◽  
Gutta Percha ◽  
Long Time ◽  
Color Reactions

Abstract THE present paper was suggested by a recent publication of Pauly on the same subject, who applied the well known sterol reactions of Hesse, Liebermann, Tschugajeff, etc., to the hydrocarbons of rubber and gutta-percha. These reactions depend either upon the action of concentrated H2SO4 on chloroform solutions of the substances in the presence or absence of acetic anhydride (Liebermann, Burchard and Hesse reactions) or other solvents, or condensation reagents are used, such as acetyl chloride and zinc chloride by Tschugajeff, and acetic acid with arsenic trichloride by Kahlenberg, and trichloroacetic acid with a trace of formaldehyde by Godoletz. All the known sterol reactions take place also with rubber or gutta-percha, with the appearance of intense red or violet colorations of varying stability, the color depending in part upon the quality and in part upon the purity of the samples. The Burchard reaction in particular is very sensitive in these respects. Thus with rubber purified with alkali by the Pummerer method, the color is a Bordeaux red which does not change for a long time, whereas solutions of unpurified rubber change rapidly, a change which is rightly ascribed by Pauly to relatively rapid oxidation in the presence of oxidation products in the case of the unpurified rubber.

Photochemical reactions of azo compounds. VII. Studies of the photochemical reactions of azobenzene under various acidic conditions

1966 ◽  
Vol 19 (8) ◽  
pp. 1445 ◽  
Author(s):  
GE Lewis ◽  
RJ Mayfield
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Sulphuric Acid ◽  
Photochemical Reaction ◽  
Acetyl Chloride ◽  
Photochemical Reactions ◽  
Aluminium Chloride ◽  
Azo Compounds ◽  
High Yield ◽  
Acidic Conditions

An investigation has been made of the photochemical and dark reactions of azobenzene in acetic acid-ferric chloride and acetic acid-aluminium chloride mixtures for comparison with the corresponding reactions of azobenzene in sulphuric acid. The photochemical reactions resulted in cyclodehydrogenation of azobenzene to benzo[c]cinnoline, and small quantities of reduction products of azobenzene were also isolated. The formation of reduction products was again observed in the dark reactions, but there was no sign of cyclodehydrogenation. The significance of these observations is now discussed. Irradiation of azobenzene in acetyl chloride, or in acetic anhydride containing hydrogen chloride, resulted in a novel photochemical reaction in which NN?-diacetyl-4-chlorohydrazobenzene was formed in high yield.

CATALYZED NITRATION OF AMINES: VI. THE NITRATION OF DI-n-OCTYLAMINE

1948 ◽  
Vol 26b (3) ◽  
pp. 271-283 ◽  
Author(s):  
K. K. Carroll ◽  
George F Wright
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Hydrogen Chloride ◽  
Nitro Compound ◽  
Acetyl Chloride ◽  
Nitration Product ◽  
By Products

The yield of purified dioctylnitramine from di-n-octylammonium chloride is low and the crude nitration product is badly contaminated with by-products which contain halogen. Since dioctylamine can be nitrosated, acetylated, chlorinated, and p-toluenesulphonated with ease it is considered that the low yield of nitro compound is owing to decomposition of the dioctylchloramine which is intermediate during the nitration process. A mechanism for this decomposition is suggested on the basis of the products isolated from treatment of the chloramine with hydrogen chloride, acetyl chloride, acetic acid, or acetic anhydride.

Ring Contractions of 3-Azido-4H-quinolizin-4-ones and 3-Azido-4H-azino[1,2 - x]pyrimidin-4-ones: a Novel Approach to 3-Aminoindolizines and their Aza Analogues

2008 ◽  
Vol 61 (2) ◽  
pp. 107 ◽  
Author(s):  
Simon Rečnik ◽  
Anton Meden ◽  
Branko Stanovnik ◽  
Jurij Svete
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Trifluoroacetic Anhydride ◽  
Reaction Products ◽  
Thermal Transformations ◽  
X Ray Diffraction ◽  
Ring Contraction ◽  
X Ray ◽  
Novel Approach

Thermal transformations of 3-azido-4H-quinolizin-4-ones 4a,b and 3-azido-4H-azino[1,2–x]pyrimidin-4-ones 4c,d, available from the corresponding heteroarylamines 2a–d, were studied. The reaction products were mostly dependent on the solvent. Thus, heating of 3-azido-1-cyano-4H-quinolizin-4-one (4a) in toluene afforded 2-(pyridin-2-yl)fumaronitrile 5a, whereas 3-amino-1-cyano-4H-quinolizin-4-one (8) was obtained on treatment of 4a in a mixture of toluene and trifluoroacetic anhydride. However, heating of 4a in acetic anhydride and in acetic acid resulted in a ring contraction to produce 3-(diacetylamino)indolizine-1-carbonitrile 6a and 3-(acetylamino)indolizine-1-carbonitrile 7a, respectively. Similarly, ring contractions took place on heating ethyl 3-azido-4-oxo-4H-quinolizin-1-carboxylate 4b and 3-azido-4H-azino[1,2–x]pyrimidin-4-ones 4c,d in acetic anhydride or acetic acid to produce the N-acetylated 3-aminoindolizine derivatives 6b, 7b and 3-aminoimidazo[1,2–x]azine derivatives 6c,d in 30–89% yields. The structures of compounds 5–8 were determined by NMR spectroscopy and X-ray diffraction.

An unusual reaction of a bridged triterpenoid α-diketone with acetic anhydride

1991 ◽  
Vol 56 (12) ◽  
pp. 2917-2935 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Miloš Buděšínský ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Spectral Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Condensation Products ◽  
Unsaturated Lactones ◽  
C Nmr

3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) reacts with acetic anhydride in pyridine under very mild conditions affording β-lactone IVa and γ-lactones Va and VIIa as condensation products. On reaction with pyridine, lactones Va and VIIa undergo elimination of acetic acid to give unsaturated lactones VIIIa and IXa, respectively. Similarly, the condensation of 20β,28-epoxy-21,22-dioxo-18α,19βH-ursan-3β-yl acetate (IIIb) with acetic anhydride leads to β-lactone IVb and γ-lactone Vb; the latter on heating with pyridine affords unsaturated lactone VIIIb and 21-methylene-22-ketone Xb. The structure of the obtained compounds was derived using spectral methods, particularly 1H and 13C NMR spectroscopy; structure of lactone IVa was confirmed by X-ray diffraction.

Coulometric generation of acetylions by oxidation of mercury in acetic anhydride and in acetic acid/acetic anhydride mixture

1988 ◽  
Vol 212 ◽  
pp. 73-79 ◽  
Author(s):  
V. Vajgand ◽  
R. Mihajlović ◽  
Lj. Mihajlović ◽  
V. Joksimović
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride
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