Synthesis of Tetradecano‐14‐lactone by Ring Enlargement The aldehyde 3, prepared by ozonolysis of 2‐allyl‐2‐nitrocyclododecanone, gave the ring‐enlargement product 5(85%) by treatment with (i‐Bu)~2~AlH. Its transformation to the tetradecano‐14‐lactone (8) __via__ the aldol ester 6 and other routes
Synthese von Makrocyclen durch Ringerweiterung von 14gliedrigen cyclischen Imiden
✍ Scribed by Thomas Koch; Vassil I. Ognyanov; Manfred Hesse
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- German
- Weight
- 430 KB
- Volume
- 75
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Synthesis of Macrocyles by Ring Enlargement of 14‐Membered Cyclic Imides
In the presence of a base, cyclododecanone derivative 2, activated in α‐position by an allyloxycarbonyl group, underwent ring enlargement with isocyanates to give 14‐membered imides (Schemes 1–3). Cleavage of the activating group gave new 14‐membered imides which could be transformed by further ring‐enlargement reactions into new macrocyclic compounds.
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nil Ether wird filtriert und im Vakuum eingedampft. Chromatographie des Rohproduktes (1.3 g vom Fp=96 'C) an 100 g Kieselgel Woelm 0.05-0.2 mm (Saule 50 x 3 cm) mit 200 ml Essigester ergibt 0.9 g (68%) (46) als gelbe Kristalle vom Fp= 114°C. Synthese von (IOa)["l: Die Losung von 700 mg (46) in 30 m
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