The 4-Homoadamantyl cation. III. Sulfuric acid catalyzed rearrangement of 4-homoadamantanol-5-13C
The 4-Homoadamantyl cation. III. Sulfuric acid catalyzed rearrangement of 4-homoadamantanol-5-13C
复制标题
4-高金刚烷基阳离子。
DOI：
10.1021/jo00866a021
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发表时间：
1976
期刊：
影响因子：
--
通讯作者：
E. Pretsch
中科院分区：
文献类型：
--
作者：
K. Mlinaric;Z. Majerski;E. Pretsch
结果4-高金刚烷酮-5-13 C经LiAlH 4还原得到4-高金刚烷醇-5-13 C（lb）。11在相同的操作条件下记录的标记的（Ib）和未标记的（Ia）4-高金刚烷醇的13 C NMR谱的比较表明，在Ib的合成过程中没有发生标记混乱;标记仅位于5位。(The实验部分详细讨论了4-高金刚醇的~（13）C NMR谱。质谱分析表明13 C富集为7.5 db 1%。在室温下，在戊烷存在下，将醇1与浓硫酸搅拌几分钟。分离戊烷层，蒸发溶剂，得到40%的粗产物混合物，将其通过GLC分析。GLC分析表明，
Results4-Homoadamantanol-5-13C (lb) was obtained by L1AIH4 reduction of 4-homoadamantanone-5-13C. 11 Comparison of 13C NMR spectra of thelabeled (lb) and unlabeled (la) 4-homoadamantanol, recorded under identical operating con-ditions, showed that no label scrambling had occurred dur-ing the synthesis of lb; the label was located exclusively at position 5.(The 13C NMR spectrum of 4-homoadamanta-nol is discussed in detail in the Experimental Section.) Mass spectrometric analysis indicated a 13C enrichment as 7.5 db 1%.Alcohol 1 was stirred with concentrated sulfuric acid in the presence of pentane for a few minutes at room temperature. The pentane layer was separated and the solvent evaporated to yield 40% of a crude productmixture which was analyzed by GLC. GLC analysis indicated the presence