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Error in proc. on rh's page

Started by Bandil, February 05, 2003, 12:03:00 PM

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Bandil


https://www.thevespiary.org/rhodium/Rhodium/chemistry/red-al.nitrostyrenes.html




On the page in the experimental section there is stated:

Typically, a solution of the substituted benzaldehyde (1 mmol) and NH4OAc (1.25 mmol) in nitroethane was refluxed for the specified time. The mixture was cooled immediately in liquid N2 or Acetone-solid CO2, diluted with CH2Cl2, and filtered while cold. Solvent was removed in vacuo, and the remaining beta-nitrostyrene was recrystallized by known procedures6.


AFAIK the given procedure would give the corresponding nitropropene and not the nitrostyrene...

pHarmacist

Nitromethane would yield nitrostyrene...


Rhodium

It is no error, phenyl-2-nitropropene is beta-methyl-beta-nitrostyrene so calling it a beta-nitrostyrene is just being vague, not wrong. You could say "nitroalkene" too, being even more unspecific as to exactly what compound is being discussed.

Just take a look in Pihkal, where Shulgin refers to substituted phenyl-2-nitropropenes as "nitrostyrenes" all the time.

Bandil