The delepine does not work well on for the preparations of amines from secondary halides. Primary halides yes, or beta-keto halides maybe, but secondary halides no.
Best not to waste time messing around with halogenations/substitutions on dillapiole.
The halogenation step will only work well in DMSO, otherwise you will get some cyclic furapiole type compound. Although not noxious, DMSO don't smell great to work with (like garlic). Smell sticks around for ages if you are not using it in a fume-hood.
The substitution step for secondary halides does not work according to most people who have tried it.
The halogenation step will only work well in DMSO, otherwise you will get some cyclic furapiole type compound.
It also works well with HBr(g) in DMF. (see Ind. J. Chem. 258 (1986) p 368-372 and p 1150-1154, claims 80% yield of 2-bromodillapiol). I've tried this w home-made HBr(g) in not-so-anhydrous DMF and TLC showed positive results.
However, an Gabriel attempt which followed (using K-phtalimide in DMSO) and subsequent reduction to the phtalide w NaBH4 and acidic hydrolysis failed, only a tinyu amount of DMMDA-2 was isolated.
I have serious doubts about the credibility of the DMMDA-2 via Delepine write-up by Egotrip, not the least about the claimed yield.
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DMF and TLC showed positive results.