Is this a procedure for the productio of the 2-bromo or dibromo compound?
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I think your reference is going to be very much like this one: Kropp, P.J., K.A. Daus, M. W. Tubergen, et al., J. Am. Chem. Soc., 1993, 115, 3071.
Surface-mediated reactions. 3. Hydrohalogenation of alkenes.
I had a discussion on the old board with someone about it. The article uses HCl in CH2Cl2 with silica or Al2O3 as the catalyst. The yields are excellence from what I remember, and react time quick. It seemed to me that the addition of water really fucked things up though. I could be wrong, maybe someone should check out that article agian and post it for good measure, maybe some can get some use out of it.
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Y E S !!! DMF is it!
And CHCl3 doesn't sound too bad either, at least for the phenols. Guess it will work just the same.
;D
"Attempts to induce direct cyclisation of 12-15 by Adams method did not succeed due to the facile fission of the methylenedioxy group under HBr-AcOH treatment. However, the methylenedioxy group was stable upto 2hr in the presence of dry HBr in non-polar solvents such as CHCl3 ....."
That means forget about AcOH/HBr! It won't work.
Thanks Gnasher!
Some one should check out that reference that I posted earlier.
It looks like it will add some more good info to the table. Some one should also scan or quote that other article I'm interested in it and I'm sure Rhodium would be interested as well...
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If you would react the 2-bromopropene with methylamine, you would get an enamine, which would rearrange to the imine, right?
http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)
lugh, the graphical version has got to bee better. I suppose those of us who grew up on Classics Illustrated versions of Ivanhoe and Treasure Island, just don't have the attention span to keep imagining these anomolous heterocyclic ring clotures looping themselves through all their acrobatics. Still, I'm glad the authors are trying to do something useful about all those useless constituents in the oil of Indian dill: "furapiole derived from dillapiole, a waste product from oil of Anethum sowa Roxb".
It is certainly a shame, that this waste product dillapiole, forms the majority constituent of the essential oil of the otherwise useful herb Matico. Other Piper species have useful substances in their essential oils, but this Piper aduncum, also known as Piper angustifolium, and by no less than twenty-five (!) other Latin binomials all referring to this one plant, is accursed by having an essential oil nearly all composed of this same waste product. No other plant has this useless dillapiole as a majority constituent, though Anethum sowa is blighted with a lot of it.
Gottlieb et al. (1981) studied the main components of the Brazilian varieties P. aduncum var. aduncum and P. aduncum var. cordulatum finding dillapiole as 74.5% and 88.4% respectively.
Gottlieb, O.R. M. Koketsu, M.T. Magalhães, J.G.S. Maia, P.H. Mendes, A.I. da Rocha, M.L. da Silva & V.C. Wiiberg. 1981. Oleos essenciais da Amazônia VII. Acta Amazonica 11: 143-148.
Gupta et al. (1983) investigated the composition of the essential oil of the fresh leaves of the plant collected in Panama finding dillapiole (90%) as majority component.
Gupta, M.P. T.D. Arias & R.M. Smith. 1983. The composition of the essential oil of Piper aduncum L. from Panamá. Rev. Latinoamer. Quím. 14: 36-37.
We might put Devakumar and Mukurjee on the job, of contorting the molecules of Matico pepper, in such fashion that vast areas of tropical America might become bug free for a long time.
turning science fact into <<science fiction>>