Chromogenic Reactions of Tertiary Amines with Polycarboxylic Acids and Acetic Anhydride: Carbon Suboxide as the Reactive Species in the Malonic Acid Reagent

1987 ◽  
Vol 76 (10) ◽  
pp. 834-838 ◽  
Author(s):  
Kenneth A. Connors ◽  
Agber Ifan
Keyword(s):  
Acetic Anhydride ◽  
Malonic Acid ◽  
Reactive Species ◽  
Tertiary Amines ◽  
Carbon Suboxide ◽  
Polycarboxylic Acids ◽  
Acid Reagent

A Novel SN1 Displacement: The Reaction of Tertiary Amines with Acetic Anhydride

1971 ◽  
Vol 49 (20) ◽  
pp. 3348-3351 ◽  
Author(s):  
R. P. Mariella ◽  
K. H. Brown
Keyword(s):  
Acetic Anhydride ◽  
Experimental Results ◽  
Methyl Ethyl ◽  
Tertiary Amines

The action of actic anhydride on tertiary amines at reflux may cause the displacement of one of the R groups from the amine. The groups which are displaced are benzyl, t-butyl, benzhydryl, trityl, and cinnamyl; the groups which are not displaced are methyl, ethyl, n-butyl, phenyl, α-naphthyl, iso-propyl, allyl, and propargyl. An SN1 mechanism with special steric requirements is consistent with the experimental results.

Comment: Concerning the Cleavage of Tertiary Amines With Acetic Anhydride

1973 ◽  
Vol 51 (13) ◽  
pp. 2177-2179 ◽  
Author(s):  
R. P. Mariella ◽  
K. H. Brown
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Methyl Acetate ◽  
Tertiary Amines

The failure of methyl-substituted tertiary amines to yield methyl acetate on cleavage by acetic anhydride indicates that the mechanism proposed by Gol'dfarb and Belen'kii cannot be correct. The results of cleavage of cinnamyldimethylamine are offered as support for the mechanism proposed by Mariella and Brown. Catalysis by acetic acid is not considered to be important.

Comment: Concerning the Paper of R. P. Mariella and K. H. Brown "A Novel SN1 Displacement: The Reaction of Tertiary Amines with Acetic Anhydride"

1973 ◽  
Vol 51 (13) ◽  
pp. 2174-2176 ◽  
Author(s):  
Ya. L. Gol'dfarb ◽  
L. I. Belen'kii
Keyword(s):  
Acetic Anhydride ◽  
Similar Data ◽  
Tertiary Amines

The remarks on the paper of Mariella and Brown (1) concern three points: (1) some similar data from the literature were not mentioned; (2) the mechanism proposed does not take into account the possibility of catalysis of the reaction; and (3) the interpretation of the process as SN1 displacement is not compatible with known data.

The Raman and infra-red spectra of carbon suboxide

1954 ◽  
Vol 223 (1153) ◽  
pp. 251-266 ◽  
Keyword(s):  
Raman Spectrum ◽  
Raman Spectra ◽  
Malonic Acid ◽  
Mass Spectra ◽  
Linear Molecule ◽  
Molecular Symmetry ◽  
Carbon Suboxide ◽  
Photoelectric Recording ◽  
Infra Red

The infra-red and Raman spectra of carbon suboxide have been redetermined since earlier data did not permit an unequivocal decision as to the molecular symmetry. The infra-red spectrum of the gas was measured over the range 275 to 4600 cm -1 using a Perkin-Elmer spectrometer. The Raman spectrum of the liquid (at — 90° C) was investigated using a photoelectric recording spectrometer constructed in this laboratory. No trouble was experienced with decomposition of the sample. The purity of the suboxide which was prepared from malonic acid was carefully checked by following changes in the infra-red and mass spectra at various stages of the purification. In this way several bands previously attributed to the suboxide were shown to be due to impurities. Details of a normal co-ordinate treatment are given, and with its aid all the observed bands are given satisfactory assignments on the basis of a linear molecule, symmetry D ∞λ . This necessitates the postulation of one infra-red active fundamental at about 198 cm -1 . Though this lies outside the region investigated here it has recently been observed by O’Loane in the course of investigations on a series of compounds in the far infra-red.

Über die Umsetzung von Amidoximäthern mit Malonsäuren in Acetanhydrid / The Reaction of Amidoxime Ethers with Malonic Acids in Acetic Anhydride

1972 ◽  
Vol 27 (10) ◽  
pp. 1169-1171 ◽  
Author(s):  
Erich Ziegler ◽  
Alkis Argyrides ◽  
Wilfried Steiger
Keyword(s):  
Acetic Anhydride ◽  
Malonic Acid ◽  
Boiling Point

Amidoxime Ethers react with malonic acid in acetic anhydride at 20° to pyrano-pyrimidones (1 a- d), however, with monosubstituted malonic acids acetoxy-pyrimidones (2 a- f) are formed at the boiling point.

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