[Seanlet]

Other than US Patent Application 'U2 2010/0191000' Methos for Synthesizing an N-unsubstituted or N-substituted Aziridine' & US 9,988,349 Direct Stereoselective Synthesis of unprotected aziridines from Olefins', I cannot find any papers that convert a non-terminal alkene (like cyclopropene) to N-methyl aziridines.

The reagent that seems the most specific and the most useful is o-(2,4-dinitrophenol)-n-methylhydroxyamine (CAS 38100-39-9).

I am considering this as an intermediate in the production of 1-propenyl-2-methylamine cyclopropene.

For anyone wondering, using trimethylamine as solvent and propenyl chloride as reagent (the HCl will quickly producing trimethylamine hydrochloride) LOOKS like an efficient route. Most routes proceed via the epoxide but trans isomers can be an issue i.e. harder to extract the isomer that is wanted.

[wildfyr]

Methyl sulfonyl azide+alkene+heat? Sulfonyl nitrenes are known to do alkene insertion to make aziridines pretty well. Don't know about methyl sulfonyl azides though, I've usually seen the phenyl.

[Seanlet]

I appreciate your input. I have come across such agents but producing the N-methyl in the 1 step is a big plus. I'm also pretty keen on exploiting what looks like a useful, non-toxic alternative.... but see me in 4 months, getting your route working ;-

[Seanlet]

BTW What I am actually trying to do is to open 1-phenyl-cyclopropene so it has a -OH at the 1 position & -NCH3 at the 2 position. Then the OH is esterified.. the patent route goes through epoxide so I'm looking for a better method for scaling. Esterification is acid chloride in triethylamine so the N isn't added to....

[wildfyr]

Ah I think I misread your post. The method I suggested would give you the methyl sulfonamide, with an aziridines on the nitrogen side. This is not your desired product. My apologies.

I'll think on this some more.