Daphuk_up (Hive Bee) 03-15-04 01:55 No 495164				Today's Half Formed Thought - Nitroethane
						SWID has been trying to "think outside the box", in middle management parlance.  Here is a few of the ideas for nitroethane he has come up with: First. Interesting link http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0139 at rhodium's page for the conversion of phenylamines to benzaldehydes via the diazonium salt.  Can the diazonium salt be oxidised, say with O3, permanganate, or H2O2, to the nitro compound?  Is the diazo group stablizied by its proximity to the benzene ring, such that a similiar reaction could not be performed on ethyl amine?  (Oh, or methylamine, with intent to react as reported to acetaldehyde?)(EDIT: The diazonium salt formation also requires NaNO2 unfortunately, but in a 1:1 molar ration with substrate.  If the proposed route above worked and turned out to be very efficient, this wouldn't be a problem.  Otherwise, probably not worth it.) Second. This is absurdly dangerous, but SWIDs curiosity will at least let him think (dream) about it.  Alkyl Isocyanates.  Say, in particular the Ethyl variety, exposed to strong oxidation in an aprotic enviroment.  Result in the release of CO2, plus the formation of the nitro compound.  Hmm, probably would require a catalyst of some sort.  Perhaps copper or a compound thereof? Drug Chemists are Ta to a good Sm.
		Rhodium (Chief Bee) 03-15-04 14:42 No 495267				diazo chemistry
						Can the diazonium salt be oxidised, say with O3, permanganate, or H2O2, to the nitro compound?  Not to my knowledge. Is the diazo group stablizied by its proximity to the benzene ring, such that a similiar reaction could not be performed on ethyl amine? That is unfortunately the case. However, ethylamine can be oxidized to nitroethane using a range of different oxidizers, UTFSE for references. The Hive - Clandestine Chemists Without Borders