- α-Methoxylation of Unsaturated Carbonyl Compounds
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α-Methoxylation of enals or enones can be performed in high yield by a simple one-pot reaction sequence: Bromination of unsaturated hydrazones, HBr-elimination, and addition of methanol leads to the formation of β-bromo-α-methoxy hydrazones (11), which af
- Feuerer, Albert,Severin, Theodor
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p. 6026 - 6029
(2007/10/02)
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- Electrophilic β-Bromination and Nucleophilic α-Methoxylation of α,β-Unsaturated Carbonyl Compounds
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Oximes 29a,b, semicarbazones 11a-d, dimethylhydrazones 4, and hydrazones 23a-c of unsaturated aldehydes and ketones are brominated at the β-carbon by an addition-elimination sequence ( 21a,b, 13a-d, 7, and 27c, respectively.) When unsaturated ketone hydrazones are treated with bromine and methanol the α-methoxy-β-bromo derivatives 35a-c are obtained, which after hydrolysis and hydrobromic acid elimination give α-methoxy substitution products 36a-c of the starting compounds.
- Fischer, Hans,Klippe, Michael,Lerche, Holger,Severin, Theodor,Wanninger, Gabriele
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p. 399 - 404
(2007/10/02)
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