THE PRINCIPAL CONFORMATIONS OF SOME ORTHO-SUBSTITUTED DIPHENYL ETHERS

1964 ◽  
Vol 42 (11) ◽  
pp. 2549-2559 ◽  
Author(s):  
W. D. Chandler ◽  
W. MacFarlane Smith ◽  
R. Y. Moir
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Hydrochloric Acid ◽  
Conformational Isomers ◽  
Ultraviolet Spectra ◽  
Diphenyl Ethers ◽  
Nuclear Magnetic

A study of the nuclear magnetic resonance, infrared, and ultraviolet spectra showed that some doubly and triply ortho-substituted diphenyl ethers adopt, principally but not exclusively, the "H-inside" conformation, while the quadruply ortho-substituted 7-(4′-carbomethoxy-2′,6′-dinitrophenoxy)metameconine (V) adopts the "methoxy-inside"conformation. Interconversion of conformational isomers is extremely fast. Reduction of methyl 4-methoxy-3-nitrobenzoate with tin and hydrochloric acid gave methyl 3-amino-2-chloro-4-methoxybenzoate.

SYNTHESIS OF 1-ARYL SUBSTITUTED 9H-PYRIDO[3,4-b]INDOLES

1965 ◽  
Vol 43 (8) ◽  
pp. 2251-2253 ◽  
Author(s):  
W. A. Skinner ◽  
R. M. Parkhurst
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Hydrochloric Acid ◽  
Reaction Conditions ◽  
Aryl Group ◽  
Nuclear Magnetic Resonance Spectra ◽  
Substituted Benzaldehydes ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

A series of 1-aryl substituted 9H-pyrido[3,4-b]indoles (1,2,3,4-tetrahydro-β-carbolines) were synthesized by cyclization of tryptamine with a number of substituted benzaldehydes in the presence of hydrochloric acid. Four modifications of reaction conditions were found necessary in order to obtain the desired products containing a variety of substituents on the 1-aryl group. Nuclear magnetic resonance spectra of the products enabled definitive assignment of structure.

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