two tequila...three techkilla........
FLOOR!(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000470560-file_6ju6.gif)
One sentence solidifies what Ibee's taken 1000, 6000word posts to convey!
Only time and moderate heat will give pure product in high yields
Will miracles never cease?(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000470560-file_fstm.gif)
Peace (https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000470560-file_epdk.gif)of the REaction
Have FUN-Bee SAFE
No, that is completely incorrect. Only time and moderate heat will give pure product in high yields
Thats not true though. And Rhodium of all people should know beter. Just look at all of the CTH methods. They deal with converting the pfed into some kinda ester (in this case a halo analogue), then hydrogenating it. Same concept here.
I wasn't saying convert the pfed to iodoephedrine and then run it through to get best quality product. I was saying this as maybe a way to get best quality product QUICKER.
I see no difference in what SWIM proposed than say converting it to a sulfate ester and hydrogenating with Pd/C. Just we are converting it to the iodo ester, and reducing via HI.
I can only think of HI(aq), PI3, (CH3)3Si-I and possibly PPh3/I2 as being viable iodination reagents.
NaBH4 in diglyme (yes, only in that solvent) will also reduce iodides to the hydrocarbon.
Selective Reductions. XI. The Reaction of Sodium Borohydride with Alkyl Halides under Solvolytic Conditions.
Harold M. Bell and Herbert C. Brown
J. Am. Chem. Soc. 88, 1473-1477 (1966) (https://www.thevespiary.org/rhodium/Rhodium/pdf/nabh4-diglyme.dehalogenation.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/nabh4-diglyme.dehalogenation.pdf)
Abstract
In nonionizing solvents, secondary and tertiary alkyl halides react with sodium borohydride only slowly, in many cases yielding the olefin, rather than the desired saturated hydrocarbon. However, the addition of water to produce typical solvolyzing conditions brings about a rapid reaction, providing the corresponding hydrocarbon in good yield, along with the concomitant formation of the alcohol and the olefin as the usual solvolytic products. Evidence is presented which indicates that the mechanism of the reduction involves the trapping of the intermediate carbonium ions formed in the solvolysis. Consequently, the reaction should be useful, both synthetically, to convert reactive alkyl halides and their derivatives to the corresponding hydrocarbons, and mechanistically, to trap carbonium ions in investigations of their nature. A number of synthetic applications is described.