Anomeric conformations of six-membered cyclic aminoxyl radicals with a β-alkoxyl substituent

✍ Scribed by Yong-Kang Zhang; Edward G. Janzen; Yashige Kotake

• Book ID: 102952505
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 522 KB
• Volume: 33
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260331323

✦ Synopsis

Abstract

The addition reactions of CH~3~(CH~2~)~3~O^·^, (CH~3~)~2~CHCH~2~O^·^, (CH~3~)~2~CHCH~2~CH~2~O^·^, (CH~3~)~3~CO^·^ and (CH~3~)~2~C(CN)O^·^ radicals to a novel six‐membered cyclic nitrone, 6,6‐dimethyl‐3,4,5,6‐tetrahydropyridine N‐oxide (M~2~PyO), generate the corresponding 6‐alkoxyl‐2,2‐dimethylpiperidine‐1‐oxyl aminoxyl (nitroxide) spin adducts. In benzene solution at room temperature, the preferential conformation of these spin adducts appears to be the anomeric conformer with the alkoxyl group in the axial position according to EPR spectroscopic conformational analysis of these aminoxyls. The anomeric effect in these aminoxyls might be the combination of electrostatic and molecular orbital interactions.