Reaction of 1,3-Disubstituted Acetone Derivatives with Pseudohalides: A Simple Approach to Spiro[4.4]nonane-Type Bis-Oxazolidines and -Imidazolidines (Bicyclic Carbamates, Thiocarbamates, Ureas, and Thioureas)
✍ Scribed by Robert Saul; Thorsten Kern; Jürgen Kopf; István Pintér; Peter Köll
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 281 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Prochiral 1,3-dihydroxyacetone forms racemic oxazolidine-with monocyclic by-products, but the spirobisimidazolidinone is accessible by reaction of 1,3-and oxazoline-type spiro[4.4]nonanes upon reactions with potassium (thio)cyanate and cyanamide. In contrast, 1,3-dichloroacetone with urea. The resolution of the racemic spiro-bisoxazolidinethione 2a was achieved by using brucine diaminoacetone yields only the corresponding spirobisimidazolidinethione under similar conditions together as the resolving agent. 2a was treated with o-chlorobenzyl chloride to give bis-al-Carl-von-Ossietzky-Strasse 9Ϫ11, D-26111 Oldenburg, kylated 5. Again we observed a tautomerization, but this Germany