Position of the cyclopropane ring in aromadendrene

✍ Scribed by L. Dolejš; F. Šorm

• Publisher: Elsevier Science
• Year: 1959
• Tongue: French
• Weight: 182 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99426-2

✦ Synopsis

IN 1953, Birch and Lahey' suggested for aromadendrene two alternative structures I and II with the cyclopropane ring in different pceitione, Ae aromadendrene on dehydrogenation affords S-guajazulene only, Birch et al, in their recent paper,2 prefer formula I. In view of the speculative character of this argument, we considered it worthwhile to establiah a conclusive proof of the position of the three-membered ring in aromadendrene. We, therefore, carried out the degradation of aromadendrene which enabled ua to decide definitely in favour of structure I. Apoaromadendrone (III)3 on treatment with perphtalic acid end subsequent hydrolysis of the resulting lactone afforded hydroxy acid IV, m.p. 122.5', [c]: + 6.3' (methanol, c, 3.15), I.R.X_ (dioxan): 1736 cm" (OH) and 3490 cm" (OH). Found: C, 69.771 H, 10.14. C14H2403 requires: C, 69.96; H, 10.0%. The proof that the tertiary carbon atom wan oxidized by Bayer-Villiger procedure has been brought forward by subsequent oxidation of substance IV to the known keto acid C14R2203 (oxime m.p. 16S").l