Solvolysis of [3-13C]-3,4-dimethyl-4-homoadamantyl p-nitrobenzoate. Comparison of the barriers to the Wagner-Meerwein rearrangement of the secondary and tertiary 4-homoadamantyl cations

Add time:08/31/2019    Source:sciencedirect.com

The trifluoroethanolysis of [3-13C]-3,4-dimethyl-4-homoadamantyl p-nitrobenzoate gave 3,4-dimethyl-4-homoadamantene (10), 3-methyl-4-methylenehomoadamantane (11), and trifluoroethyl ether (12a) in the ratio 62:36:2 at 40 °C. The 13C labels were exclusively distributed at the positions C(3) and C(4), and redistribution ratios were 92.8:7.2 in 10, 93.3:6.7 in 11, and 61.1:38.9 in 12a. Comparison of these results with those for the solvolysis of secondary [3-13C]-4-homoadamantyl p-toluenesulfonate suggests that the barrier to the Wagner-Meerwein rearrangement of the tertiary 4-homoadamantyl cation is higher than that of the secondary cation by at most 3.3 kcal mol−1.

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