𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A 1H and 13C NMR study of N-formylmorphinans and their 6,14-bridged derivatives; Comparison with N-Me and NH analogues

✍ Scribed by J. T. M. Linders; M. A. Prazeres; T. S. Lie; L. Maat

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
470 KB
Volume
27
Category
Article
ISSN
0749-1581

No coin nor oath required. For personal study only.

✦ Synopsis

The 'H NMR and I3C NMR spectra of N-formylated morphinans were compared with those of the N-methyl and N-demethyl analogues. The magnitude of the changes in chemical shift of C-9, C-16 and C-10 depended crucially on the nature of the substituent at nitrogen. For the 6a,l4aethenoisomorphinans and 6~,14/?-ethenomorphinans, the proton chemical shifts of the 6,14-etheno bridge across ring C are differently affected by the nitrogen atom. In the 6a,14a-ethenoisomorphinans, the vinylic proton shifts are found between 65.3 and 5.9, whereas in the 68,148ethenomorphinans these proton signals are found downfield from 66.0. A similar, but opposite, anisotropy effect of the nitrogen is observed for the 88-proton. These results are important for the elucidation of the structures of these types of compounds. KEY WORDS 6a,l4a-Ethenoisomorphinan 68,14fi-Ethenomorphinan Nitrogen anisotropy Face selectivity of the Diels-Alder reaction * Chemistry of the Opium Alkaloids, Part XXX. For Part XXIX, see Ref. 13.

📜 SIMILAR VOLUMES

Furoxan rearrangement of some pyridofuro
Furoxan rearrangement of some pyridofuroxan derivatives studied by 1H, 13C, 14N, 15N and 17O NMR spectroscopy
✍ P. Cmoch; B. Kamieński; K. Kamieńska-Trela; L. Stefaniak; G. A. Webb 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 107 KB 👁 1 views

Pyridofuroxan ([1,2,5]oxodiazolo [3,4-b]pyridine 1-oxide) undergoes isomerization between the N1oxide and N3-oxide forms which can be observed by the 1 H, 13 C and 15 N NMR spectroscopy but not by 14 N and 17 O NMR at ambient and low temperatures. The rearrangement becomes slower at low temperatures

A 1H, 13C and 15N NMR investigation of t
A 1H, 13C and 15N NMR investigation of three substituted DMAN derivatives and their monoprotonated salts
✍ Mariusz Pietrzak; Lech Stefaniak; Alexander F. Pozharskii; Valery A. Ozeryanskii 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 52 KB 👁 1 views

We report a 1 H, 13 C and 15 N NMR investigation of one symmetrically substituted 2,7-dichloro and two unsymmetrically substituted 2-chloro and 4-bromo DMAN [1,8-bis(dimethylamino)naphthalene] proton sponges and their protonated salts. From a consideration of the NMR data reported we conclude, that

N,N-Disubstituted α-Amino-α,β-unsaturate
N,N-Disubstituted α-Amino-α,β-unsaturated Aldehydes and their Derivatives: 1H and 13C NMR Study
✍ Alexander Yu. Rulev; Alexander S. Mokov; Leonid B. Krivdin; Natalia A. Keiko; Mi 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 212 KB 👁 1 views

1H and 13C NMR spectra of N,N-disubstituted a-amino-a,b-unsaturated aldehydes and their azomethines and enammonium salts were studied. The spectra reÑect the degree of p-p conjugation between the nitrogen lone pair and the p-electrons of the carbon-carbon double bond. In this respect, the title 2-am

1H and 13C NMR study of copteroside E de
1H and 13C NMR study of copteroside E derivatives
✍ Carlos M. Cerda-García-Rojas; Graciela Zamorano; María Isabel Chávez; César A. N 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 181 KB 👁 2 views
1H, 13C and 15N NMR spectral assignments
1H, 13C and 15N NMR spectral assignments of adenosine derivatives with different amino substituents at C6-position
✍ Silvana Casati; Ada Manzocchi; Roberta Ottria; Pierangela Ciuffreda 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 94 KB

## Abstract The complete ^1^H, ^13^C and ^15^N NMR signals assignment of adenosine derivatives differently substituted at C^6^‐position was achieved using one‐ and two‐dimensional experiments (gs‐COSY, gs‐NOESY, gs‐HSQC and gs‐HMBC). Copyright © 2011 John Wiley & Sons, Ltd.