Effects of annulation on the mass spectral behaviour of monosubstituted bicyclo[4.3.0]-3-nonenes and bicyclo[4.3.0]-3,7-nonadienes
✍ Scribed by František Tureček; Vladimir Hanuš
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- English
- Weight
- 566 KB
- Volume
- 13
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
Abstract
The mass spectra of the title compounds differ considerably depending on the annulation of the bicyclic skeleton. For a series of alkyl derivatives the cis‐annulated compounds show a higher abundance of the products due to the retro Diels‐Alder cleavage than the corresponding trans isomers. The cis‐annulated esters and alcohols lose a molecule of ethanol and water, respectively, more easily than the corresponding trans isomers. Effects of conformation and configuration are discussed.
📜 SIMILAR VOLUMES
## Abstract Carbon‐13 NMR signal assignments of some bicyclo[4.3.0]nonan‐4‐ones (hydrindanones) and bicyclo[4.4.0]decal‐4‐ones are reported.
## Abstract 2‐(__tert__‐Butyl)‐3,7‐dehydrotropone (7‐(__tert__‐butyl)bicyclo[3.2.0]hepta‐1(7),2,4‐trien‐6‐one; **1**) was found to dimerize reversibly to **2A** by [2 + 4]‐cycloaddition/cycloreversion reaction. The equilibrium lies on the side of the highly strained dimer **2A** in the solid state,