Abstract
To provide an opportunity for X-ray analysis of an unsubstituted fenestrane, one of the ring-fusion carbon atoms was replaced with a nitrogen atom to facilitate salt formation; the key strategic step to the first 1-azafenestrane (see scheme) involves the tandem [4+2]/[3+2] cycloaddition of a nitrocyclopentene with butyl vinyl ether. The adduct with borane provided crystals suitable for X-ray analysis, which revealed the planar deformation of the central carbon atom to be modest (116.1 and 116.6°).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4122-4125 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 41 |
| Issue number | 21 |
| DOIs | |
| State | Published - Nov 4 2002 |
Keywords
- Anti-van't Hoff/Le Bel compounds
- Cycloaddition
- Fenestrane
- Nitroalkene
- Polycycles
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)