NMR examination of tricyclo[4.2.0.01,3]octane
โ Scribed by William B. Smith; Udo H. Brinker
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 230 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0749-1581
No coin nor oath required. For personal study only.
โฆ Synopsis
The structure of the strained tricyclic hydrocarbon tricyclo [ 4.2.0.0'~~ I octane was determined by a combination of 1D and 2D NMR involving both proton and carbon signals. The stereochemistry of the molecule was determined by NOE difference spectroscopy. The assigned structure corresponds to the thermodynamically more stable fruns form as ascertained by molecular mechanics calculations.
๐ SIMILAR VOLUMES
Regioselective generation of the C(2)-carbocation a of tricyc10[4.2.2.0',~]decane (1) by treatment of both corresponding epimeric alcohols 5 and 6 with BF, and trapping the rearranged tricy~lo[S.3.0.O~~~]decan-7-yl carhocation b with Et,SiH as hydride-ion donor (ionic hydrogenation) gives the corres
downfield. Thus on complex formation of (/), additional shielding and deshielding effects occur which can be explained in terms of a diamagnetic ring current in complex (2). We therefore propose the homoaromatic structure (2a) for the complex. Further support for this assignment comes from the fact