The Vespiary

The Hive => Chemistry Discourse => Topic started by: Tezcatlipoca on June 26, 2002, 03:36:00 PM

Title: in-situ borane generation in TBME
Post by: Tezcatlipoca on June 26, 2002, 03:36:00 PM

borane-ether complexe can be generated in situ by the addition of I2 to NaBH4 in Et2O. Could a similar complex be made by the addition of I2 to NaBH4 in tert-butyl methyl ether? Would this complex reduce nitrostyrenes to the corresponding amine?

Thanks in advance,
Tezcatlipoca

Title: You can also use dimethylsulfate, and even H2SO4 ...
Post by: Osmium on June 26, 2002, 05:38:00 PM

You can also use dimethylsulfate, and even H2SO4 instead of I2.

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I'm not fat just horizontally disproportionate.

Title: Thankyou Osmium. I was aware that a variety of ...
Post by: Tezcatlipoca on June 27, 2002, 01:14:00 PM

Thankyou Osmium. I was aware that a variety of reagents - I2, H2SO4, Me2SO4, TMSCl, BF3-Et2O, etc. However, I have never seen an example of this done in a solvent other than THF or Et2O. So the question is, will TBME work as a solvent for this reaction, and if so will it affect yields? I have searched the Hive, Google, and other places for more info on this but have found nothing relevant. Please help if you can.

Thanks,
Tezcatlipoca

Title: I don't know. The ethers form some complex with ...
Post by: Osmium on June 28, 2002, 01:57:00 AM

I don't know. The ethers form some complex with the BH3, and for some reason (steric hinderance) TBME might not do that. Or maybe it does, I really don't know.

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I'm not fat just horizontally disproportionate.