Photochemistry of bicyclo[3.3.1]nonanes having two functional groups at 3,7-positions
✍ Scribed by Takasi Mori; Kwang Her Yang; Kôichi Kimoto; Hitosi Nozaki
- Book ID
- 104249065
- Publisher
- Elsevier Science
- Year
- 1970
- Tongue
- French
- Weight
- 127 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Bicyclo(3.3.l)nonane system prefer6 twin chair conformation (1) in which functional groups at 3,7-position6 are extremely close to each other to induce facile tranaannular interaction. Ionic cyclisation of this type of compound8 ie well known to form adamantans derivatives (2.1, but few has been recorded on photochemical reaction6 (3).
📜 SIMILAR VOLUMES
The Huang-Minlon reduction of 7a-hydroxymethylbicyclo[3.3.11nonan-3-one (1) gave 7B-methylbicyclo[3.3.llnonan-36-01 (21, a product formed as a result of the transannular 1,6-hydride shift enforced by relief of the steric constraint in the system. Another example of the intramolecular hydride transfe
nonan-9-ones, 1-3, l-alkoxycarbonyl derivates, 4, 5 and aand fl3methyl-3-azabicyclo[3.3.1]nonan-9-ols, 6, 7, have been studied by means of the molecular mechanics (MMX) method and ~H, t3C-NMR spectroscopy. Experimental data fit well with theoreticalcalculations. It is found that the conformational b