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A Further Synthetic Approach to the Adamantane Isomer 2, 5-Trimethylenenorbornane (Tricyclo [5.3.0.03,9]decane, 4-Homotwistbrendane)

✍ Scribed by Hans-Ruedi Känel; Camille Ganter

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
252 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A further synthetic approach to 2, 5‐trimethylenenorbornane (1; tricycle [5.3.0.0^3,9^]decane, 4‐homotwistbrendane), a member of the «adamantaneland», is described starting from methyl 5‐oxo‐2endo‐norbornanecarboxylate (5). The required C2‐chain was introduced by a Wittig‐Horner reaction and the ring closure of the trimethylene bridge achieved by an acyloin condensation.

📜 SIMILAR VOLUMES

The Novel Adamantane Isomer 2,5-Trimethy
The Novel Adamantane Isomer 2,5-Trimethylenenorbornane (Tricycio-[5.3.0.3,9]decane, 4-Homotwistbrendane)
✍ Hans-Ruedi Känel; Hans-Georg Capraro; Camille Ganter 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 299 KB

## Abstract A synthesis of the novel C~10~H~16~ hydrocarbon 2,5‐trimethylenenorbornane (tricyclo[5.3.0.0^3,9^]decane, **1**), one of the 19 members of the ‘adamantaneland’, and its __Lewis__‐acid‐catalyzed rearrangement is described.