mmda via pseudonitrosite

[grellobanans]

Does isomyristicin react in the same fashion as asarone,anethole, etc.? pseudonitrosite -> nitropropene, and then reduction to ketone, and then standard reductive amination with MeNH2?
Also, in general, how toxic is the NO2 gas formed if working on a small scale?

[Rhodium]

Yes, that is a very good route, isomyristicin will react just like all the other propenylbenzenes.

NO₂ is always very toxic, but if you are working on a small scale, say ~5-10g isomyristicin), then you will have no problems containing the gas in the reaction apparatus - nothing is toxic to you as long as you don't come into contact with it.

[grellobanans]

What are the expected yields with isomyristicin?

Swim had the impression that the NO2 gas would lower yield, that's why it is better to purge the vessel with inert gas.
Hmmm...by the way, has anyone ever tried using CO2 from an OTC fire extinguisher? Would it keep oxygen sensitive compounds from reacting?

[Rhodium]

The expected yield of an unknown compound... It is unknown, I think. But it should be in the same ballpark as the other pseudonitrosites, why wouldn't it?

If you read up on the pseudonitrosite threads, you'll see that NO2 gas is only formed if you add the acid too fast to the NaNO2/alkene mixture, if you add it slow enough (dropwise), then the alkene will have time to react with the gas before it evolves from the solution.

CO2 is of no use here, that makes no sense at all.

[catastrophe]

SWIM has heard that it works very very poor on isomyristicin. SWIM does not have the literature with him/her now, but if recollection is correct it was like ~10%, maybe less after hydrolysis. No known reason was given. Perhaps a better method might be

https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitryliodide.html

[GC_MS]

According to Enrico Rimini, one of the Italian Godfathers of the Ancient Chemistry Goodies, the nitrosite is obtained in more or less 80% yield.

Dopo dodici ore di riposo nel limite di separazione degli strati etereo ed acquoso, si ha il nitrosito in grumtti bianco citrini, perfettamente essenti da resina tanto che basta decantare lo strato etereo, lavare con acqua, filtrare e lavare su filtre successivamente con alcool ed etere per avere il prodotto pronto per l'analisi, con un rendimento che oscilia intorno all'ottanta per cento del calcolato. Mamma Miracoli!

E Rimini. Sulla miristicina. Gazz Chim Ital 35(I) (1905) 406-416.

No yields are given for the beta-nitrostyrene.

[Antibody2]

run the rxn in a side arm flask with a hose from the sidearm going out a window, then NO2 isn't an issue.