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- W2108157601 abstract "The behavior of the exo and endo isomers of 7,7-dimethyltricyclo[3.3.1.0 2,4 ]nonan-6-one (5, 6) under strongly basic conditions (t-BuOH/t-BuOH/185 °C) has been examined. In sharp contrast to their [3.2.1.0 2,4 ] analogs, the endo isomer is stable while the exo readily rearranges to 8,8-dimethyltricyclo-[4.3.0.0 2,4 ]nonan-7-one (16). Experiments were carried out in tert-butyl alcohol-O-d 1 to establish the sites of deuterium incorporation in the initial ketones as well as the relative rates and stereoselectivities of the exchange processes. Ketones 5 and 6 were prepared through ring expansion by ketonization of cyclopropoxides generated from the [3.2.1.0] homologs; the stereochemistry of these ketonizations was established by 2 H labelling." @default.
- W2108157601 created "2016-06-24" @default.
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- W2108157601 date "1985-06-01" @default.
- W2108157601 modified "2023-09-27" @default.
- W2108157601 title "13C nuclear magnetic resonance studies. 114. An examination of the [3.3.1.0] → [4.3.0.0] rearrangement via β-enolization and H/D exchange in tricyclic ketones" @default.
- W2108157601 doi "https://doi.org/10.1139/v85-213" @default.
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