𝔖 Bobbio Scriptorium
✦   LIBER   ✦

1,2endo-Trimethylenenorbornane. A novel isomer of adamantane

✍ Scribed by Franz Josef Jäggi; Camille Ganter

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
386 KB
Volume
63
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

An easy approach to the novel adamantane isomer 1,2__endo__‐trimethylenenorbornane (2) is described. Starting from a mixture of pent‐4‐ynylcyclopentadienes 3 the tricyclic monosaturated key intermediate 5 was prepared by intramolecular cycloaddition (→4) and subsequent regioselective reduction of the C(5), C(6) double bond. The title hydrocarbon 2 was obtained from 5 upon stereoselective hydrogenation by diimide. In addition specifically deuteriated analogues of 2 were prepared applying dideuteriodiimide. Compound 2 rearranged to 2__endo__, 6__endo__‐trimethylenenorbornane (4‐homobrendane, 10) in sulfuric acid as well as with aluminium bromide in carbon disulfide.

📜 SIMILAR VOLUMES

The Adamantane Rearrangement of 1,2endo-
The Adamantane Rearrangement of 1,2endo-Trimethylenenorbornane. Preliminary communication
✍ Alfred Michael Klester; Franz Josef Jäggi; Camille Ganter 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 105 KB 👁 2 views

## Abstract 1,2__endo__‐Trimethylenenorbornane **(1)** in the presence of aluminium bromide in carbon disulfide at −60° isomerizes at a much higher rate than its 2__exo__‐isomer **2** to 2__endo__, 6__endo__‐trimethylenenorbornane **(3)** as the sole product. By consequence, the hydrocarbon **2** b

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 👁 1 views

## 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.

The adamantane rearrangement of 1,2-trim
The adamantane rearrangement of 1,2-trimethylenenorbornanes. Part IV. Hydride-ion abstraction in 1,2-exo-trimethylenenorbornane
✍ Alfred Michael Klester; Camille Ganter 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 371 KB 👁 2 views

4, 'Adamantaneland': a set of 19 isomeric C,,H,,-hydrocarbons [2-4]. Compounds 4 6 correspond to the general formula B D (R' = D, R2 = R3 = R4 = H) of Scheme 3 in [I]. ' 1 k , h = log ([Alt/[AlJ/log ([BIJBIJ or kA/k, = {log[(lxt)/(lxo)] + log([ -s)}/{log(x,/x,) f log(1 -s)), where xO and x, represen

The Adamantane Rearrangement of 1,2-Trim
The Adamantane Rearrangement of 1,2-Trimethylenenorbornanes. III. AlBr3-catalyzed rearrangement to 2,6-trimethylenenorbornane
✍ Alfred Michael Klester; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 483 KB 👁 2 views

## Abstract From treatment of D‐labelled 1, 2__exo__‐, 1, 2__endo__‐ and 2__endo__, 6__endo__‐trimethylene‐norbornane (**1, 2** and **3**, resp.) with aluminum bromide in carbon disulfide, the evidence is gained that a degenerate rearrangement is involved in the admantane rearrangement of both **1*

A Further Synthetic Approach to the Adam
A Further Synthetic Approach to the Adamantane Isomer 2, 5-Trimethylenenorbornane (Tricyclo [5.3.0.03,9]decane, 4-Homotwistbrendane)
✍ Hans-Ruedi Känel; Camille Ganter 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 252 KB 👁 2 views

## 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‐Horn