𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesen von Tricyclo [5.2.1.04,8]decan (2-Homobrendan)

✍ Scribed by Franz Josef Jäggi; Peter Buchs; Camille Ganter

Book ID
102858480
Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
936 KB
Volume
63
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Syntheses of Tricyclo [5.2.1.0^4,8^]decane (2‐Homobrendane)

Three different approaches to tricyclo [5.2.1.0^4,8^] decane (5) (and derivatives thereof), one of the 19 isomeric hydrocarbons of the ‘adamantaneland’, are described: (1) Cyclization of properly functionalized bicyclo [3.2.1]octanes as 32(cyclialkylation), 40+42 (thermocyclization) and 44+45 (photocyclization); (2) Silver‐(I)‐ion catalyzed rearrangement of 5,7‐ and 5,10‐Dehydroprotoadamantane (63 and 64, respectively) yielding tricyclo[5.2.1.0^4,8^]dec‐2‐ (39) and ‐5‐ene (59), respectively; (3) Thermal eliminative rearrangement of the 10__endo‐p__‐toluenesulfonate and ‐methanesulfonate of protoadamantane (71 and 72) and protoadamant‐4‐ene (76 and 77), respectively, yielding tricyclo [5.2.1.0^4,8^]dec‐2‐ene (39) and ‐2, 5‐diene (15), respectively.

📜 SIMILAR VOLUMES

The Adamantane Rearrangement of Tricyclo
The Adamantane Rearrangement of Tricyclo[4.2.2.01,5]decane to Tricyclo[5.3.0.04,8]decane
✍ Kanai L. Ghatak; Camille Ganter 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 German ⚖ 345 KB 👁 1 views

Regioselective generation of the C(2)-carbocation a of tricyc10[4.2.2.0',~]decane (1) by treatment of both corresponding epimeric alcohols 5 and 6 with BF, and trapping the rearranged tricy~lo[S.3.0.O~~~]decan-7-yl carhocation b with Et,SiH as hydride-ion donor (ionic hydrogenation) gives the corres

Synthesis and hydroboration/oxidation of
Synthesis and hydroboration/oxidation of tricyclo(5.2.1.04,10)dec-8-ene-2,5-dione(bis-acetal): new synthetic entry to tricyclo(5.2.1.04,10)decane-2, 5, 8-trione
✍ Elena Carceller; M.Llutsa Garcaía; Felix Serratosa; Manuel Font-Altaba; Xavier S 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 784 KB

Tricyclo(5.2.1.04~10)dacane-2,S,8-trions (4) has bssn aynthasized from the cortssponding bis-acetal of the unsaturated diketons 20 by a hydroborationloxihationfdaprotsction saquence.