- The Pummerer-type reaction mediated ring-opening of 2-alkyl substituted 1-[(2-methoxyethoxy)methoxy]-2-(phenylsulfinyl)cyclopropanes
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α-Lithiated 1-[(2-methoxyethoxy)methoxy]-2-(phenylsylfinyl)cyclopropane reacted smoothly with alkylating agents to afford the corresponding α-alkylated cyclopropylsulfoxides, which underwent the Pummerer-type reaction mediated ring-opening at low temperature (-78°C) by employing TFAA/Pri2NEt/CH2Cl2 to give mixtures of β-(phenylthio)-α,β- and γ,δ-unsaturated aldehydes.
- Pohmakotr, Manat,Moosophon, Panawan,Pisutjaroenpong, Somchai,Tuchinda, Patoomratana,Reutrakul, Vichai
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p. 4389 - 4391
(2007/10/03)
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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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- Reactions of Unsaturated Aldehyde Dimethylhydrazones with Electrophilic Reagents
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Crotonaldehyde dimethylhydrazone (1) is substituted at C-3 by electrophiles such as chlorine, bromine, iodine, arylsulfenyl chloride, phenylsulfinyl chloride, and nitronium tetrafluoroborate to form the products 10a-c, 18a,b, 25, and 26.In contrast, from
- Severin, Theodor,Wanninger, Gabriele,Lerche, Holger
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p. 2875 - 2885
(2007/10/02)
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- Metal-Catalyzed Stereospecific Michael Reaction Equivalent
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The addition of nucleophiles to vinyl sulfide-allylic acetates mediated by (?-allyl)palladium intermediates has been shown to occur exclusively on the allyl terminus remote from sulfur, thereby effecting the equivalent to a Michael reaction.Due to the int
- Godleski, Stephen A.,Villhauer, Edwin B.
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p. 2246 - 2252
(2007/10/02)
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- Oxidation of Alcohols with tert-Butyl Hydroperoxide and Diaryl Diselenide
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Treatment of alcohols with tert-butyl hydroperoxide in the presence of diaryl diselenide in refluxing benzene gives the corresponding aldehydes or ketones.Although some allylic alcohols undergo oxidation in the presence of 10-15 mol percent of bis(p-chlorophenyl) diselenide, use of 0.5 equiv of bis(2,4,6-trimethylphenyl) diselenide gives satisfactory results in almost all cases.The procedure can be used for selective oxidation of alcohols bearing a phenylthio or phenylseleno group, which usually survives the reaction conditions to give the corresponding carbonyl compounds.
- Kuwajima, Isao,Shimizu, Makoto,Urabe, Hirokazu
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p. 837 - 842
(2007/10/02)
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- SELECTIVE OXIDATION OF HYDROXY GROUPS OF PHENYLTHIO AND PHENYLSELENO ALCOHOLS
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Various kinds of alcohols bearing phenylthio or phenylseleno moiety were converted into the corresponding carbonyl compounds in good to excellent yields by treating with dimesityl diselenide and tert-butyl hydroperoxide.
- Shimizu, Makoto,Urabe, Hirokazu,Kuwajima, Isao
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p. 2183 - 2186
(2007/10/02)
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