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- W2950202801 abstract "A new and effective method for the preparation of a variety of olefinic carboxamides 6a–k and N-(4-methylphenyl-sulfonyl) carboxamides 7a–d is described. The reaction of aryl and alkyl isocyanates 4a–c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a–e and di-1-alkenyldibutylstannanes 2a–c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a–k or the N-(4-methylphenyl-sulfonyl)-substituted olefinic carboxamides 7a–d in good yields. The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system. In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation." @default.
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- W2950202801 date "1994-06-01" @default.
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- W2950202801 title "Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β‐unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates" @default.
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- W2950202801 doi "https://doi.org/10.1002/cber.19941270625" @default.
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