New N-permethylations and introduction of deuterium labelled methyl groups into primary and secondary amines
✍ Scribed by Angelo G. Giumanini; Giancarlo Verardo; Maria H. Gei; Lucia Lassiani
- Book ID
- 102374738
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- French
- Weight
- 466 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
The extension of the N-permethylation reaction of amines to aromatic amines with strong electron withdrawing substituents i n 0-and ppositions is reported. A comparison of t h i s method with other "best" l a s t step synthetic methods reported in literature is given. The reaction could be extended to the syntheses of N-permethyl-derivatives of amines of the type CH3-nDn by use of formaldehyde, dideuteroformaldehyde , sodium borodeuteride and -hydride. Label conservation in the reaction is complete: the final step i n the reaction involves H-(or D-) transfer from the reducing agent to a reactive species. The MS of the labelled compounds revealed extensive label excange i n the ionization chamber. A new homogeneous procedure for the N-permethylation, especially suited for l a r g e r scale preparations, is described.