Derivatives of morphine: the structure of pentachloro-oxy- and -ethoxycodides; an unusual addition reaction to an aromatic ring

1968 ◽  
pp. 774 ◽  
Author(s):  
U. Eisner ◽  
T. J. Batterham ◽  
U. Weiss ◽  
Isabella L. Karle
ChemInform ◽  
2003 ◽  
Vol 34 (34) ◽  
Author(s):  
Sho-ichi Iwamatsu ◽  
Fumiaki Ono ◽  
Shizuaki Murata

2021 ◽  
Vol 316 ◽  
pp. 75-80
Author(s):  
Oleg Kh. Karimov ◽  
Galina Yu. Kolchina ◽  
Eldar M. Movsumzade

In the framework of method of the B3LYP hybrid density functional and the restricted Hartree-Fock method, quantum-chemical calculations of model compounds of lignin, i.e. derivatives of p-hydroxycinnamic alcohol were carried out. The structures and reactivity of coumaric, coniferyl and synapol alcohols were studied. Quantitative characteristics of the reactivity of these acids are given. It is found that the electronic structure of lignin is determined primarily by the charge distribution in its structural phenylpropane unit. In the molecules of all model compounds of lignin, the center for nucleophilic attack is the carbon of aromatic ring (E-ring) with a hydroxyl group, and in the molecule of synapol alcohol, this center is also the carbon of the aromatic ring (E-ring) with a methoxy group. In all three compounds, a center with an increased electron density appears on the Сβ carbon atom.


1971 ◽  
Vol 24 (6) ◽  
pp. 1237 ◽  
Author(s):  
RC Cambie ◽  
DR Crump ◽  
WA Denny ◽  
TJ Fullerton

The stereochemistry of 6-bromo-7-oxo derivatives of diterpenoids possessing an aromatic ring c is discussed. Nan-stereospecific bromination of 7-oxo diterpenoids occurs for compounds with an unactivated aromatic ring provided that no methoxycarbonyl substituent is at C 4. It also occurs for a C 19 acetate providing an activating substituent is present at C 12, but not for compounds with a C 4 methoxycarbonyl group even if they possess a C 12 activating substituent. The assignment of configuration of 6-bromo substituents from nuclear magnetic resonance and nuclear Overhauser effect data is examined and limitations to the use of optical rotatory dispersion curves are discussed.


2018 ◽  
Vol 71 (9) ◽  
pp. 690 ◽  
Author(s):  
Asha M. D'Souza ◽  
Daniel J. Rivinoja ◽  
Roger J. Mulder ◽  
Jonathan M. White ◽  
Adam G. Meyer ◽  
...  

A study of the reactivity of a non-stabilised azomethine ylide, derived from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, with nitro-substituted isatoic anhydrides was undertaken. N-Methyl-4-nitroisatoic anhydride underwent a 1,3-dipolar cycloaddition reaction exclusively at the isatoic anhydride C1-carbonyl group, followed by decarboxylative rearrangement to yield a benzo-1,3-diazepin-5-one derivative. In contrast, N-methyl-5-nitroisatoic anhydride underwent competing cycloaddition processes to the isatoic anhydride C1-carbonyl group and to the nitro-substituted aromatic ring. The dearomative addition reaction resulted in the formation of novel tetracyclic products.


2013 ◽  
Vol 70 (1) ◽  
pp. 60-66 ◽  
Author(s):  
Ray Jones

The structures of 6-nitro-1,3λ4δ2,5,2,4-trithiadiazepine [C2HN3O2S3, (1)], 6,7-dinitro-1,3λ4δ2,5,2,4-trithiadiazepine [C2N4O4S3, (2)], 1,3λ4δ2,5,2,4-trithiadiazepine-6,7-dicarbonitrile [C4N4S3, (3)] and 7-acetyl-1,3λ4δ2,5,2,4,6-trithiatriazepine [C3H3N3OS3, (4)] presented here include the most precise determinations of these seven-membered 10 π-electron aromatic ring systems published to date. Both (2) and (3) are sited around crystallographic twofold axes with half a molecule per asymmetric unit. Comparison with other published derivatives of these rings reveals the effect of substituents on bonding, conformations and intermolecular interactions, including π-stacking. The deformation density analysis of (2) is consistent with the expected bonding electron density from other theoretical and experimental studies.


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