Versuche zur Herstellung eines «Bis(triasterans)» und Synthese des heterocyclischen (Tricyclo[4.4.1.01,6]undeca-3,8-dien-11,11-dimethyl)sulfits
✍ Scribed by Richard Neidlein; Karl Friedrich Wesch
- Publisher
- John Wiley and Sons
- Year
- 1983
- Tongue
- German
- Weight
- 504 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Tentative Synthesis of ‘Bis(triasterane)’ and Synthesis of the Heterocyclic (Tricyclo[4.4.1.0^1,6^]undeca‐3,8‐diene‐11,11‐dimethyl)sulfite
The synthesis of the bis(triasterane) (1) has been tried; the reaction of ‘isotetraline’ (1,4,5,8‐Tetrahydronaphthalene; 2) with diazomalonate yielded the tricyclic systems 5 and 6, and not 4. Hydrolysis of 5 gave the monocarboxylic acid 7, and not the dicarboxylic acid 9. The latter could be obtained from the dibromoderivative 8, but 9 couldn't be converted to the acyl chloride 10. The reduction of 9 with LiAlH~4~ yielded the crystalline diol 11, which was cyclized with SOCl~2~ to the heterocycle 12. The spectral data of the new compounds 5, 6, 7, 11 and 12 are reported and discussed.