BF3 + NaBH4 -> BH3 to reduce 3,4 mdns
Since BBr3 is know to cleave methoxy groups, I assume it can also cleave methylenedioxygroups, which leads me to believe that using the BF3 + NaBH4
combo to produce in situ BH3, with the goal of using the BH3 to reduce 3,4-methylenedioxynitrostyrene to 3,4-methylenedioxyphenylethylamine, to not be
feasible, as the methylene dioxy bridge would be cleaved resulting in the phenolic product.
Can anyone comment on this speculation? Something that gives me a glimmer of hope that it will work is the Synth. Comm. 15(9), 843-847, 1985 paper,
where they reduce a nitro propene that has a 3,4 diethoxynitropropene to the respective alkyl amine. I know there is a difference between the
methylenedioxy group and an ethoxy group however; this is where my question comes from.
[Edited on 17-9-2014 by zephler1]
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