カンフェンとトリシクレンの四酢酸鉛酸化

抄録

The oxidation of camphene [1] and tricyclene [2] was investigated with lead tetraacetate and subsequent hydrolysis. The oxidation of [1] gave camphenilanaldehyde [3], R-homo-camphenilone [4], exo-R-homocamphenilol [5], endo-R-homocamphenilol [6], 3-endo-hydroxy-R-homocamphenilone [7], 3-exo-hydroxy-R-homocamphenilone [8], and camphene glycol [9]. A similar oxidation of [2] resulted in three products: camphor [10], tricyclenyl alcohol [11], and nojigiku alcohol [12]. Their structure and stereochemistry were determined on the basis of MS, IR, ¹³C-NMR, and ¹H-NMR spectra by the variations in the contact shift of each proton with shift reagent Eu (dpm)₃. Compound [7] and [8] possessed a mild nojigiku-like odor.