Isomeric_Fred
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NaBH4/CuSO4 nitro reduction success!!
NaBH4/CuSO4 system in EtOH/H2O was given another shot.
phenylnitroalkane was reduced in reflux to yield roughly 50% of amine. More details to come.
:-D
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Tyr
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congratulations!
I can´t wait to read a detailed report.
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dextro
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your NaBH4/CTH writeup is great, so why another route ? is there a difference in bioassaying ?
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a-SalviaLover
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where is it?
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Isomeric_Fred
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the problem with nabh4/cth is that sometimes the nabh4/nitro form a complex nitronate which traps nitroalkene. then it is not fully reduced and when
later you are trying to break the complex there is some reaction which is happening catlayzed by the GAA which makes the nitroalkene/nitroalkane to
react and make a colored solution which is hard to work with to give good yields. this happens mostly with specific nitroalkenes but might happen with
all if u are not careful. this is the reason for the trying of new methods.
the CuSO4/NaBH4 has been tried on nitroalkane several times and found succesful, but now we are working on nitrolkane to hydroxylamine reduction in
one pot with BF3xEt2O/NaBH4, which works like a charm. more on the cupric reductions to come soon.
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Isomeric_Fred
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update - still we have not got consistent results from cupric sulfate/sodium borohydride reduction. we have posted our results and complete write up
for BF3xEt2O/NaBH4 here - https://sciencemadness.org/talk/viewthread.php?tid=7190
When we have more progress on the cupric sulfate issue we will post it.
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