Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Stable Sulfur Ylides. II. : Syntheses of Stable Sulfonium Allylides and Oxosulfonium Allylides
MITSUAKI WATANABETOSHIO KINOSHITASUNAO FURUKAWA
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JOURNAL FREE ACCESS

1975 Volume 23 Issue 1 Pages 82-85

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Abstract
Reaction of dimethyloxosulfonium-(I), dimethylsulfonium-(II), and tetramethylenesulfonium benzoylmethylide (III) with 2, 2-diacetyl- and 2-acetyl-2-ethoxycarbonyl-1-ethoxyethylene (VI), in the presence of triethylamine afforded the corresponding 1-benzoyl-3, 3-diacetyl- and -3-acetyl-3-ethoxycarbonylallylides (VII, VIII, and IX) in a good yield. Similar treatment of ethoxycarbonylmethyldimethyl- and ethoxycarbonyltetramethylene sulfonium bromides (IV and V) with VI gave the corresponding allylides (X and XI). These 3, 3-diacetylallylides (VII and VIII) and 3-acetyl-3-ethoxycarbonylallylides (X) were hydrolyzed to the corresponding 3-acetylallylides (XII, XIII, and XIV) by treatment with dilute hydrochloric acid under a mild condition.
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© The Pharmaceutical Society of Japan
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