Tetrahedron Letters p. 7147 - 7150 (1997)
Update date:2022-07-30
Topics:
Porter, John M.
Xuan, Xiangyang
Blackman, Burchelle
Hsu, Daniel
Fry, Albert J.
Anodic oxidation of 1,2-bis-(trimethylsilyl)-1,2-diphenylethane in methanol affords a 65:35 mixture of 1,2-dimethoxy-1,2-diphenylethane (dl:meso = 10:1 and diphenylacetaldehyde dimethylacetal. The results can be interpreted in terms of a 1,2-diaryl-2-methoxyethyl cation, which can undergo either nucleophilic attack by solvent or rearrangement to a 2,2-diaryl-1-methoxyethyl cation. Experiments testing the generality of the reaction are described.
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