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- W1979640873 abstract "A kinetic study in FSO3H/SbF5 reveals that the 1-methyl-2-methyleneaziridinium ion 4 rearranges in a first order reaction to the ring-opened enammonium ion 6. At temperatures below 80° this process takes place via isomerisation of the methyleneaziridinium ion to an intermediary cyclopropaniminium ion 5. At higher temperatures the direct conversion 4 → 6 - which is negligible in the lower temperature region - must also be taken into account (cf. Scheme 4). 1,1-Dimethyl-2-methyleneaziridinium fluorosulfate undergoes a similar heterocyclic - homocyclic ring rearrangement in FSO3H, but higher temperatures (115°) are required. The rearranged product, N,N-dimethylcyclopropaniminium fluorosulfate is much more stable than the mono-N-methyl derivative i.e. it can be heated up to 150° without decomposition. By analogy the methyleneaziridinium → cyclopropaniminium isomerisation is thought to take place via a ring-opened biradical cationic species rather than via a diamagnetic 2-(mono- or dialkylamino)allyl cation." @default.
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- W1979640873 date "2010-09-02" @default.
- W1979640873 modified "2023-10-11" @default.
- W1979640873 title "Chemistry of small-ring compounds. Part 42. The rearrangement of methyleneaziridinium ions to cyclopropaniminium ions" @default.
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- W1979640873 doi "https://doi.org/10.1002/recl.19790980303" @default.
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