Electron transfer from α-(1) or β-pinene (2), to 2,3,5,6-tetrachlorobenzoquinone generates radical cations, which are rapidly deprotonated by the semiquinone radical anion. (1S,5S)-2 is converted to (1S,5S)-1 and (1R,5R)-1 yields a dehydrogenation product, verbenene, (1R,5R)-9 with essentially quantitative retention of optical activity. The results support chiral, "ring-closed" radical cation structures in which the allylic-quaternary cyclobutane C-C bond retains a significant degree of bonding.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry