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- W2952441211 abstract "The reaction of 1-phenylallyl-lithium (1a) with optically active 2-halobutanes in ether in the presence of tetramethylethylenediamine or hexamethylphosphoramide gives exclusively 4-methyl-3-phenylhex-1-ene (5a)(coupling at the phenyl-substituted site) with essentially 100% inversion of configuration. In contrast, treatment of 1,1-diphenylallyl-lithium (1b) with (–)-2-halobutanes under the same conditions results in the formation of a mixture of 4-methyl-3,3-diphenylhex-1-ene (5b)(coupling at C-1) and 4-methyl-1,1-diphenylhex-1-ene (6b)(coupling at C-3). Moreover, C–C bond formation at the 1-position to provide (5b) is also found to proceed with complete inversion of configuration, while a small but significant loss of stereochemical integrity is observed in the case of the C-3 attack product (6b). These results suggest that a polar pathway should predominate for the formation of the C-1 attack products (5a, b), while competition between polar and single-electron-transfer processes occurs for the formation of the C-3 attack product (6b)." @default.
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- W2952441211 date "1989-11-28" @default.
- W2952441211 modified "2023-09-26" @default.
- W2952441211 title "ChemInform Abstract: Reaction of Phenyl-Substituted Allyl-lithiums with Secondary Alkyl Halides. A Polar Process versus Single-Electron Transfer." @default.
- W2952441211 cites W2089249584 @default.
- W2952441211 doi "https://doi.org/10.1002/chin.198948097" @default.
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