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The Aluminum-Bromide-Catalyzed Adamantane Rearrangement of syn- and anti-Tricyclo[4.2.1.12,5]decane

✍ Scribed by Marco Brossi; Camille Ganter


Publisher
John Wiley and Sons
Year
1987
Tongue
German
Weight
194 KB
Volume
70
Category
Article
ISSN
0018-019X

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📜 SIMILAR VOLUMES


Anti- and syn-Tricyclo [4.2.1.12,5]decan
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## Abstract The two novel tricyclic C~10~H~16~ compounds __anti__‐ and __syn__‐tricyclo [4.2.1.1^2,5^]‐ decane (**16** and **17**, respectively) were synthesized starting either from the photodimer **2** (__anti__) or the two cycloaddition products **8** (__anti__) and **9** (__syn__).

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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

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## Abstract Acid treatment of 9__exo__‐methyl‐__anti__^10,11^‐tricyclo[4.2.1.1^2,5^]deca‐3,7‐diene‐9__endo__, 10__endo__‐diol (**8**) leads to the two isomeric pentacyclic ethers **7** and **9** by intramolecular nucleophilic substitution of a protonated OH‐group with participation of a C,C‐double