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- W1967213710 abstract "1-Aza-2-azoniaallene salts 3 react with ethene, and mono- to trisubstituted electron-rich alkenes under mild conditions to afford 4,5-dihydro-3H-pyrazolium salts 4. These cycloadditions proceed with complete Markovnikov regioselectivity and retention of the configuration of the alkene. Reactions of salts 3 with norbornene afford cycloadducts without rearrangement of the norbornane moiety. According to these observations, reactions of heteroallenes 3 with alkenes are mechanistically concerted ‘reverse electron-demand 1,3-dipolar cycloadditions’. In solution 4,5-dihydro-3H-pyrazolium salts 4 with a hydrogen atom in the 5-position tautomerize to 4,5-dihydro-1H-pyrazolium salts 6. A ‘general Wagner–Meerwein rearrangement’ to the 1H-isomer 5y is observed for compound 4y. The mechanistic proposals are supported by AM1 calculations. For the salt 4r and the twofold cycloadduct 4z X-ray stuctural analyses have been performed." @default.
- W1967213710 created "2016-06-24" @default.
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- W1967213710 date "2000-01-01" @default.
- W1967213710 modified "2023-09-23" @default.
- W1967213710 title "Cycloadditions of 1-aza-2-azoniaallene ions to alkenes" @default.
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- W1967213710 doi "https://doi.org/10.1039/b006525k" @default.
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