Orientation of azide addition to homoconjugated dienes

1970 ◽  
Vol 48 (2) ◽  
pp. 345-350 ◽  
Author(s):  
R. S. McDaniel ◽  
A. C. Oehlschlager
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Double Bond ◽  
Magnetic Resonance ◽  
Transition State ◽  
Phenyl Azide ◽  
Nuclear Magnetic Resonance Spectra ◽  
Bicyclic Dienes ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The 1,3-dipolarcycloaddition of phenyl azide to bicyclic dienes 8–10 proceeds readily at the angle strained double bond to give both 1,2,3-Δ2-triazoline isomers which would result from the two possible orientations of addition. The major triazoline isomer in each case is that resulting from stabilization of the dipolar transition state by the neighboring unreactive double bond. The structures of the triazolines were deduced from their nuclear magnetic resonance spectra in CCl4, CDCl3, and C6H6.

The nuclear magnetic resonance spectra of some related alkylene-substituted diethylamines

1967 ◽  
Vol 45 (1) ◽  
pp. 21-27
Author(s):  
Morris Freifelder ◽  
Richard W. Mattoon ◽  
Russell Kriese
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Double Bond ◽  
Magnetic Resonance ◽  
Carbon And Nitrogen ◽  
Nuclear Magnetic Resonance Spectra ◽  
Tertiary Carbon ◽  
Methylene Groups ◽  
Tertiary Nitrogen ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The nuclear magnetic resonance spectra of N1, N1-diethyl-2,2-dimethylpropane-1,3-diamine (I), bis-(3-diethylamino-2,2-dimethylpropyl) amine (II) and N1-(3-diethylamino-2,2-dimethyl) propylidene-N3, N3-diethyl-2,2-dimethyl-1,3-propanediamine (III) are examined. In the spectrum of I, separate single peaks are observed for the methylene groups adjacent to the primary and tertiary nitrogen atoms. In the spectrum of II, the symmetrical secondary amine, the pair of methylene groups adjacent to the secondary nitrogen atom appears as a singlet separate from the methylene protons between the tertiary carbon and nitrogen atoms. Acetylation of I and II makes it possible to identify the methylene signals of each compound. In the spectrum of III, dissymmetry because of unsaturation [Formula: see text] is responsible for the differences in the peak positions of the signals of seemingly similar groups. This difference extends to the signals for the terminal methyl protons, which are six and seven bonds from the double bond.

The nuclear magnetic resonance spectra of the codeine isomers and their derivatives

1965 ◽  
Vol 18 (11) ◽  
pp. 1799 ◽  
Author(s):  
TJ Batterham ◽  
KH Bell ◽  
U Weiss
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Double Bond ◽  
Magnetic Resonance ◽  
Chemical Shift ◽  
Heterocyclic Ring ◽  
First Order ◽  
Nuclear Magnetic Resonance Spectra ◽  
First Order Methods ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The nuclear magnetic resonance spectra of codeine, isocodeine, pseudocodeine, allopseudocodeine, neopine, isoneopine, and some of their derivatives have been studied and the patterns produced by the protons on dl rings except the N-heterocyclic ring have been analysed by first-order methods. Allylic, homoallylic, and other long-range couplings have been observed. Differences in chemical shift between protons in different isomers have been explained in terms of the anisotropy of the double bond or the aromatic ring.

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