Compounds with bridgehead nitrogen. 56—The 1H NMR spectra and stereochemistry of some perhydrooxazolo[3,4-a]quinolines and 3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolines
✍ Scribed by Trevor A. Crabb; Geoffrey C. Heywood
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- English
- Weight
- 414 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
The configurations and preferred conformations of some perhydrooxazolo[3,4-alquinolines and of the related 3,3a,4,5-tetrahydro-1H-oxazolo[3,4-u]quinolines have been assigned on the basis of their 'H NMR spectra. Comparison of the spectra of the two sets of compounds shows the effect of replacement of the alicyclic ring in the fully reduced compounds by the aromatic ring in the 3,3a,4,5tetrahydro-lH-oxazolo[3,4-u]quinolines on the 'H NMR parameters of the NCH,O protons.
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## Abstract __cis__(4‐H,11b‐H)‐4‐Aryl‐1,6,7,11b‐tetrahydro‐2__H__,4__H__‐[1,3]oxazino [4,3‐__a__]isoquinoline and the related thiazino compound preferentially adopt in solution the O (or S) inside __cis__‐conformation in contrast to __cis__(1‐H,4a‐H)‐1‐arylperhydropyrido[1,2‐__c__][1,3]oxazine whic