2003年
Static and dynamic stereochemistry of N-(1,4-dimethyl-9-triptycyl)-hydroxylamine derivatives
Bulletin of the Chemical Society of Japan
- ,
- ,
- ,
- ,
- 巻
- 76
- 号
- 9
- 開始ページ
- 1801
- 終了ページ
- 1811
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1246/bcsj.76.1801
Static and dynamic stereochemistry of N-alkyl, O-alkyl, and N,O-dialkyl derivatives of N-(1,4-dimethyl-9-triptycyl)hydroxylamine were studied. X-ray crystallographic analysis revealed that an N-alkyl derivative adopts R*-(-sc)* conformation while N,O-dialkyl derivatives adopt R*-ap conformation. In solufion, stereomutation was almost frozen on the NMR timescale at ca. -60 °C. The same conformer as found in the crystal was the major conformer in solution in each compound, and a small amount of a second conformer was found in equilibrium with the major one for the N-alkyl and N,O-dialkyl derivatives. The stereomutation was interpreted in terms of diastereomerization and enantiomerization, and the 1H NMR lineshape analysis afforded the activation parameters for these processes.
- リンク情報
- ID情報
-
- DOI : 10.1246/bcsj.76.1801
- ISSN : 0009-2673
- ORCIDのPut Code : 51044774
- SCOPUS ID : 0141483182