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- W2146668030 abstract "Abstract Hypobromous acid addition to unsaturated steroid C-19 acids 5 and 7 involves intramolecular participation of the carboxyl group and affords bromolactones 21 and 25. The C-19 ester group in methyl esters 6 and 8 shows no participation and the addition proceeds with external nucleophile attack yielding bromohydrnis 22 and 26. By contrast, homologous C-19a methyl esters 10, 12 as well as acids 9, 11, afford bromolactones. 18O-Labeling proved that the bromolactonization in 10 and 12 took place with participation by the carbonyl oxygen. The different reactivity of the ester groups in 6, 8 and 10, 12 is due to stereoelectronic factors. Mechanistic aspects of bromolactonization in acids and esters are discussed." @default.
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- W2146668030 date "1983-01-01" @default.
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- W2146668030 title "Mechanism and structural effects in bromolactonization" @default.
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- W2146668030 doi "https://doi.org/10.1016/s0040-4020(01)88674-9" @default.
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