INVESTIGATION OF THE STRUCTURE OF 1,5-METHYLENE-QUINOLIZIDINIUM ION

1966 ◽  
Vol 44 (1) ◽  
pp. 13-22 ◽  
Author(s):  
O. E. Edwards ◽  
Gábor Fodor ◽  
Léo Marion
Keyword(s):  
Molecular Weight ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Rigorous Proof ◽  
Nuclear Magnetic Resonance Spectra ◽  
Salt Structure ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

Galinovsky observed that O-tosyllupinine (II) readily isomerized to a quaternary tosylate. Without rigorous proof he assigned to this a monomeric azetidinium salt structure. A study of the infrared and nuclear magnetic resonance spectra and molecular weight of the compound confirms the 1,5-methylene-quinolizidinium salt structure III.

Reaction of glyoxal at the ortho position of phenols. Synthesis of 5a,10b-dihydrobenzofuro[2,3-b]benzofurans and 2-(3-benzofuranyl)phenols

1967 ◽  
Vol 45 (15) ◽  
pp. 1777-1784 ◽  
Author(s):  
E. C. M. Coxworth
Keyword(s):  
Molecular Weight ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Ortho Position ◽  
Acidic Media ◽  
Nuclear Magnetic Resonance Spectra ◽  
Acid Catalyzed ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The acid-catalyzed reaction of glyoxal at the ortho position of phenols has been shown to yield, as initial products, substituted 5a,10b-dihydrobenzofuro[2,3-b]benzofurans, such structures being indicated by the nuclear magnetic resonance spectra, and confirmed in several cases by synthesis via an unambiguous route. At higher temperatures in acidic media, and in the absence of glyoxal, these initial products were converted into the corresponding 2-(3-benzofuranyl)phenols. When glyoxal was present in acidic media, the 2-(3-benzofuranyl)phenols reacted further to give unidentified products of appreciably higher molecular weight.

scholarly journals Degradation of (±)-synephrine by Arthrobacter synephrinum. Oxidation of 3,4-dihydroxyphenylacetate to 2-hydroxy-5-carboxymethyl-muconate semialdehyde

1977 ◽  
Vol 167 (1) ◽  
pp. 163-170 ◽  
Author(s):  
R K Kutty ◽  
N A Devi ◽  
M Veeraswamy ◽  
S Ramesh ◽  
P V S Rao
Keyword(s):  
Molecular Weight ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Reaction Rates ◽  
Nuclear Magnetic Resonance Spectra ◽  
Chemical Behaviour ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

1. Cell-free extracts of Arthrobacter synephrinum catalyse the oxidation of 3,4-dihydroxy-phenylacetate. 2. The product of oxidation was characterized as 2-hydroxy-5-carboxymethylmuconate semialdehyde from its chemical behaviour as well as from nuclear-magnetic-resonance spectra. 3. A 3,4-dihydroxyphenylacetate 2,3-dioxygenase (EC 1.13.11.15) was partially purified from A. synephrinum. 4. The enzyme had a Km of 25 micrometer towards its substrate and exhibited typical Michaelis-Menten kinetics. 5. The enzyme also catalysed the oxidation of 3,4-dihydroxymandelate and 3,4-dihydroxyphenylpropionate, at reaction rates of 0.5 and 0.04 respectively of that for 3,4-dihydroxyphenylacetate. 6. The enzyme was sensitive to treatment with thiol-specific reagents. 7. The molecular weight of the enzyme as determined by Sephadex G-200 chromatography was approx. 282000.

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