, then hydrolyze it to the 2-butanone with the Nef Reaction.
AFAIK, Nef rxn works only on nitroalkanes, not nitroalkenes, does it not?
I mean, if that was THAT simple - why bother w/iron in GAA or, as recently posted by outstanding Barium ;) - with SnCl2?
Just for the record - do nitrostyrenes form salts with alkali, and how stable those are?
Antoncho
Rhodium -
Condensing Benzaldehyde with 1-nitropropane was my first idea (see Post 313641 (https://www.thevespiary.org/talk/index.php?topic=12554.msg31364100#msg31364100)
(Kinetic: "Interesting!", Serious Chemistry)), but after a little research, prompted by Osmium's reply to that post, it seems that the yields for this reaction will be very low (see Pihkal #1 AEM for an examle).
I'm assuming this will be the case for all aldehydes + 1-nitropropanes, as the longer chain of the nitropropane will donate electrons to stabilise the other end of the molecule with the nitro group attached, and make it less susceptible to deprotonation (and therefore unable to react). Is this the case? Or will a suitably strong base increase the yield?
However, I have found a small note in a textbook made about the condensation of 1-nitrohexane and benzyl bromide, with THF as solvent, using butyllithium as base, and HMPA (Hexamethylphosphoramide) as what seems to be a catalyst. This is done in two steps as alkyl halides are not compatible with BuLi. I'm afraid I don't have any references for this.
Has anyone heard of a high yielding synthesis using 1-nitropropane and benzaldehyde?
Here it is: Post 317855 (https://www.thevespiary.org/talk/index.php?topic=9120.msg31785500#msg31785500)
(Barium: "Knoevenhagel-Walter; another way", Methods Discourse)
Thankyou Barium, and Rhodium. Barium, I thought I had read all of your posts, but I must have missed that one :-[ .
This is exactly what I need though, as I had a feeling there were ways to form P2B via the nitrostyrene, but didn't know where to look - TFSE didn't return much, as such a specific IUPAC name often doesn't, and I must admit I didn't know the name of the reaction...
When SWIK finally gets the time and his remaining chemicals, he will let you know the results ;D .
You say n-butylamine and cyclohexylamine will not work here, but in Rhodium's method, Post 103792 (https://www.thevespiary.org/talk/index.php?topic=7493.msg10379200#msg10379200)
(Rhodium: "Re: Piperonal ---> MDA", Chemistry Discourse), it seems to work fine.
Will cyclohexylamine therefore substitute for the n-propylamine you use in your condensation, in Post 317855 (https://www.thevespiary.org/talk/index.php?topic=9120.msg31785500#msg31785500)
(Barium: "Knoevenhagel-Walter; another way", Methods Discourse)?
OK, well obviously the original intention of this post was to make alpha-ethyl PEA and alpha-ethyl N-methyl PEA from P2B. But how about another method, partly adapted from Psycho Chemist's https://www.thevespiary.org/rhodium/Rhodium/chemistry/ppa.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/ppa.html)
, to make alpha-ethyl N-methyl PEA? I propose;
1.Acylate benzene with butyryl chloride/AlCl3
2.Add bromine as above link
3.Add alcoholic methylamine solution instead of alcoholic ammonia solution
4.Reduce using HI/red phosphorus, to give 1-phenyl-2-(N-methylamino)butane ;D
Can anyone think why this would/would not work? I expect the intermediate from step 3 (cathinone analogue) would be unstable to heat, since there is both an amine and ketone in the molecule, although in Psycho chemist's writeup there doesn't seem to be a problem. Would this intermediate ketone have to be reduced with sodium borohydride to the alcohol before attempting the red phosphorus/iodine reaction reduction of the final step?