Post 464917 (https://www.thevespiary.org/talk/index.php?topic=6355.msg46491700#msg46491700)
(Antoncho: "Thanx a lot, Imp!", Chemistry Discourse), SWIM decided to see how effective a reducing agent SnCl2 is, so a quick experiment was performed...so i'd guess that should also bee the case with aliphatic NO2's ...
Not at all Antoncho. Sn and Fe with HCl will almost always reduce a nitro compound to the amine - they are for complete reduction of aromatic/aliphatic nitro compounds. As a matter of fact, Zn and HCl will usually lead to the hydroxylamine (contrary to what you might believe).
Nitrostyrenes are a much different type of animal compared to aromatic/aliphatic nitro compounds. Yes, they will form oximes with SnCl2/Fe and HCl (of course in the acidic environment the oximes usually hydrolyse to the carbonyl compound), but nitrostyrenes also form oximes with Na2S2O4. Na2S2O4 being another reagent used to reduce nitro to amino groups. And even better, surpizingly Zn/HCl reduces nitroethenes to amines more efficiently than Al/Hg! See what a bizarre way they react? It is very difficult to predict what an effective reducing agent will be.
SWIM always wanted to give SO2(g) a try as a reducing agent. A long time ago, SWIM bubbled a solution of CuSO4/NaCl with SO2 for 15-20 minutes to obtain CuCl. It was interesting because at first, the solution became darker (a sulphur complex?), but then as more SO2 was absorbed it faded to a very light yellow with the CuCl precipitate. As expected, a drop of H2O2 on the crystals caused immediate reduction and the formation of green CuCl2. SO2 and zinc seems to form zinc dithionite as you stated Antoncho - this is promising.
So what other useful things might we due with SnCl2? A big problem with SnCl2 is that you have to bubble H2S into the solution in order to precipitate it out without causing basification (although sometimes it will form an insoluble adduct making isolation a breeze). Throw some ideas in, it will be fun to discuss.
Stratosphere:
SWIM doesn't think it would be practical as a substitute for the Al/Hg. It could probably reduce the formed imine, but it would seem a step backwards instead of forwards in regards to new synthetic pathways. Do you understand what SWIM is trying to convey?
...wait for the ricochet.
Post 392067 (missing)
(Aurelius: "P2P from Tin (II) and nitropropene", Methods Discourse) - the needed SnCl2 will be generated in situ. Just calculate the right amount of tin/HCl. The tin will dissolve readily - quicker than suspending it in conc. HCl and waiting several days... (wierd, but works!)