ACID-CATALYZED REACTIONS OF VINYL COMPOUNDS: PART III. 2,7,9,10-TETRAMETHYLANTHRACENE FROM VINYL ACETATE AND TOLUENE

1964 ◽  
Vol 42 (5) ◽  
pp. 1242-1243 ◽  
Author(s):  
J. M. Pepper ◽  
Margaret Howell ◽  
B. P. Robinson
Keyword(s):  
Vinyl Acetate ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

not available

ACID-CATALYZED REACTIONS OF VINYL COMPOUNDS: IV. MECHANISM OF FORMATION OF THE PRODUCTS OF THE REACTION OF VINYL ACETATE AND BENZENE

1966 ◽  
Vol 44 (15) ◽  
pp. 1809-1816 ◽  
Author(s):  
J. M. Pepper ◽  
B. P. Robinson
Keyword(s):  
Ethyl Acetate ◽  
Vinyl Acetate ◽  
Vinyl Chloride ◽  
Intermediate Product ◽  
Aluminium Chloride ◽  
Mechanism Of Formation ◽  
Isolation And Identification ◽  
Alkylation Of Benzene ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

In part II of this series the isolation and identification of nine products from the reaction of vinyl acetate with benzene and aluminium chloride were described. This paper presents a discussion of the mechanism of formation of these compounds.A comparison of the aluminium chloride catalyzed reactions of benzene with vinyl acetate and ethyl acetate is described. The reaction with ethyl acetate gave all the monocyclic products obtained from the reaction involving vinyl acetate, as well as m-diethylbenzene. The ratio of the ortho and para isomers of ethylacetophenone is the same in both reactions, which suggests that the same acetylating species is involved. The fact that none of the three polycyclic products is obtained from the reaction involving ethyl acetate suggests that the vinyl moiety of the ester is involved in the formation of these compounds from vinyl acetate. The use of 14C-labelled vinyl acetate confirmed the fact that the synthesis of 9,10-dimethylanthracene involved only the vinyl part of the ester.A study of the reactions of ethyl acetate and vinyl acetate with aluminium chloride showed that ethyl chloride and vinyl chloride, respectively, may be intermediates in the alkylation of benzene with these reagents. Evidence is presented that 1-phenylethyl chloride may also be an intermediate product in the reaction of vinyl acetate and benzene. 1,1-Diphenylethane is believed to be involved in the formation of 9,10-dimethylanthracene, the final step of which is thought to occur by the dehydrogenation of 9,10-dihydro-9,10-dimethylanthracene.

ACID-CATALYZED REACTIONS OF VINYL COMPOUNDS: PART I. PRELIMINARY STUDIES ON VINYL ESTERS AND BENZENE

1962 ◽  
Vol 40 (1) ◽  
pp. 122-127 ◽  
Author(s):  
J. M. Pepper ◽  
B. P. Robinson ◽  
G. W. Schwanbeck
Keyword(s):  
Vinyl Acetate ◽  
Maximum Yield ◽  
Molar Ratio ◽  
Chromatographic Study ◽  
Vinyl Esters ◽  
Mechanism Of Formation ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
High Yields ◽  
First Time

A detailed study of the nature, and the mechanism of formation, of the products of the aluminum chloride catalyzed reaction of vinyl esters and benzene has been initiated. Using vinyl acetate the formation of the previously reported acetophenone, 1,1-diphenylethane, and 9,10-dimethylanthracene has been confirmed. By means of both column chromatography and thermal distillation, a similar carbonyl-containing fraction was obtained which, as a result of a gas chromatographic study, has been shown to be a mixture of six compounds. Of these, the two major components have been identified as acetophenone and p-ethylacetophenone, the latter previously unreported as a product of this reaction.The reaction of vinyl formate and benzene has been studied for the first time. High yields of 9,10-dimethylanthracene were obtained but no carbonyl-containing compounds. A study of the effect of a variation in molar ratio of benzene to vinyl acetate indicated that a maximum yield of 9,10-dimethylanthracene was obtained using a 6:1 molar ratio.The significance of these results is discussed.A method has been devised for an improved synthesis of 9,10-dimethylanthracene. The generality of this procedure for the synthesis of other substituted polynuclear compounds is indicated.

Photoinduced rearrangement of hydroxymethylisoxazolines, a route to enaminoaldehydes

1986 ◽  
Vol 51 (10) ◽  
pp. 2167-2180 ◽  
Author(s):  
Lubor Fišera ◽  
Nadezhda D. Kozhina ◽  
Peter Oravec ◽  
Hans-Joachim Timpe ◽  
Ladislav Štibrányi ◽  
...  
Keyword(s):  
Thionyl Chloride ◽  
Quantum Yields ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Photoinduced Rearrangement ◽  
Condensed Heterocycles

3-Aryl-4-R-carbamoyl-5-hydroxymethylisoxazolines (IV) were synthesized by allowing R-NH2 amines with R = H, CH3, C3H7, C6H5C2H5, and NH2 to act on 3-(X-phenyl)-4-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazoles (III) with X = H, 4-CH3, 4-OCH3, 2-OCH3, 4-Cl, 2-Cl, 4-F, 2-F, 4-Br, 4-NO2, and 3-NO2. Exposed to radiation, the substances IV give Z-2-hydroxymethylamino-2-aryl-1-formylacrylamides (V) in good yields. The 4-Cl and 4-F substituted Z-derivatives V isomerize irreversibly to the E-derivatives VI if allowed to stand in solvent; the remaining derivatives V are stable. The quantum yields of the photoreaction are from 0.012 to 0.106 in dependence on the substituent X. In all cases where the compounds IV were used for the preparation of condensed heterocycles in conditions of acid-catalyzed reactions, lactones III were preferentially formed; the action of thionyl chloride on IV results in the formation of chloromethyl derivatives VIII, which do not undergo further cyclization.

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

2021 ◽  
Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Diazoacetate ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

Kinetic modelling of reactions for the synthesis of 2-methyl-5-ethyl pyridine

2021 ◽  
Author(s):  
Emanuele Moioli ◽  
Leo Schmid ◽  
Peter Wasserscheid ◽  
Hannsjoerg Freund
Keyword(s):  
Kinetic Modelling ◽  
Acid Catalyst ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Kinetics Of

The kinetics of the acid catalyzed reactions of acetaldehyde ammonia trimer (AAT) and paraldehyde (para) to 2-methyl-5-ethyl pyridine (MEP) in the presence of an acid catalyst were investigated systematically. A...

ChemInform Abstract: Intramolecular Acid-Catalyzed Reactions of o-Carbomethoxy-ω-diazoacetophenones.

ChemInform ◽  
1987 ◽  
Vol 18 (47) ◽  
Author(s):  
S. V. CHAPYSHEV ◽  
L. I. KIRKOVSKII ◽  
V. G. KARTSEV
Keyword(s):  
Acid Catalyzed ◽  
Catalyzed Reactions
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