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)|
|Number of pages||4|
|Journal||Angewandte Chemie - International Edition|
|State||Published - Nov 4 2002|
- Anti-van't Hoff/Le Bel compounds
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