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Reaction of Sulfoximines with Diazomalonate in the Presence of Cu-salt. A New Synthesis and Stereochemistry of Optically Active Oxosulfonium Ylids

✍ Scribed by Naomichi Furukawa; Fujio Takahashi; Toshiaki Yoshimura; Shigeru Oae


Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
224 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis


In the course of the study on the chemistry of sulfoximine, we found that CHC13 decomposes violently when it is treated with NaOH in dimethyl sulfoximine. However when the decomposition was carried out in the presence of cyclohexene, 7,7-dichlorobicycloC4.l.Olheptane was obtained only in 5% yield with a concomitant decomposition of the sulfoximine. This observation suggests that dichlorocarbene is generated during the reaction, but consumed by a competing reaction with the sulfoximine thus lowering the yield of the carbene adduct. In order to clarify the reaction of carbenes with sulfoximines, a few typical sulfoximinesl) were treated with dimethyl diazomalonate(DDM) in the presence of Cu-salt as catalyst.


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