The 4-Homoadamantyl cation. III. Sulfuric acid catalyzed rearrangement of 4-homoadamantanol-5-13C (CROSBI ID 268361)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Majerski, Zdenko ; Mlinarić-Majerski, Kata ; Pretsch, Ernoe
engleski
The 4-Homoadamantyl cation. III. Sulfuric acid catalyzed rearrangement of 4-homoadamantanol-5-13C
The rearrangement-hydride transfer reduction of 4-homoadamantanol-5-l3C in concentrated sulfuric acidpentane gave homoadamantane (2), 2-methyladamantane (3), and 4-homoisotwistane (4). The label was equilibrated over all ring carbons in each of the products but there was a small excess of the label located at the methyl group of 3. The results are interpreted in terms of a rapid degenerate rearrangement of the 4-homoadamantyl cation accompanied by rearrangements of this cation to the 2-homoadamantyl cation and an unsymmetrically bridged 2-adamantylcarbinyl cation. Therefore, l, a-carbon shifts, 1, 2-hydride shifts, and 1, 3-hydride shifts are all involved.
rearrangement-hydride transfer ; 4-Homoadamantanol ; 4-Homoadamantyl
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Podaci o izdanju
41 (4)
1976.
686-690
objavljeno
0022-3263
1520-6904
10.1021/jo00866a021