The synthesis of 3,3-dimethylmorpholine-2,5-diones 4a was achieved conveniently via the direct amide cyclization of the linear precursors of type 3, which were prepared by coupling of 2,2-dimethyl-2H-azirin-3-amines 2 with 2-hydroxyalkanoic acids 1. Thionation of 4a with Lawessons reagent yielded th
2,3,5,6-Tetramethylmorpholine: II—1H n.m.r. structural studies of the isomers of 2,3,5,6-tetramethylmorpholine
✍ Scribed by Sven Hernestam; Bertil Nilsson
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- English
- Weight
- 478 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
The structures of the six isomers of 2,3,5,6‐tetramethyl‐morpholine have been determined by means of proton nuclear magnetic resonance studies at 100 MHz. The spectra have been analysed in terms of spin–spin coupling constants and population distributions of the possible conformers at low temperatures. Also included in this paper are results from n.m.r. studies on the six 4‐benzyl‐2,3,5,6‐tetramethylmorpholine derivatives, which give information about the stereochemistry of the methyl groups α to the amine group.
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## Abstract (__R__)‐5‐(diallylamino)‐5,6‐dihydro‐4__H__‐imidazo[4,5,1‐__ij__]quinolin‐2(1__H__)‐one (__12b__) was prepared in 9% overall yield from 3‐aminoquinoline. Reaction of __12b__ in ethyl acetate with tritium gas in presence of a 5% platinum on carbon catalyst afforded a mixture of (__R__)‐5