stratosphere (Hive Bee)
03-03-04 00:59
No 492497
       henry rxn with thial...easy amphetamine?     

if one were to perform a "henry condensation" between thiobenzaldehyde ,PhC(=S)H, and nitroethane, if a decent yield of the nitro thiol would result, it would seem that this could be reduced with great ease to amphetamine, for example using urshibira Ni at low pressure.

is there any lit. examples of henry condensations with thials? 		 
 
 
 
    WizardX
(Wizard Master)
03-03-04 12:12
No 492614
       henry condensations     

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv9p0636




http://www.orgsyn.org/orgsyn/prep.asp?prep=V77P0236

  
 
 
 
    stratosphere
(Hive Bee)
03-04-04 19:57
No 492975
       but these examples all appear to be regular...     

but these examples all appear to be regular henry condensations, i was looking specifically into henry condensations between a nitroalkane and a thial (thioaldehyde). 		 
 
 
 
    moo
(Hive Bee)
03-05-04 01:35
No 493040
       Thiobenzaldehyde     

Googling for "thiobenzaldehyde" yields a hit, http://www.csj.jp/journals/bcsj/bc-cont/bc69-3.html,  where you can find a reference to a scientific article titled "Synthesis, Structure, and Some Reactions of (2,4,6-Tri-t-butyl)thiobenzaldehyde, the First Stable Aromatic Thioaldehyde" from year 1995. This, and the fact that thiobenzaldehyde cannot be found in aldrich catalogue suggest that unsubstituted thiobenzaldehyde isn't a stable compound that could be used as a reagent. An interesting idea though. smile
fear fear hate hate 		 
 
 
 
    stratosphere
(Hive Bee)
03-05-04 19:50
No 493200
       thanks moo, too bad such an appealing route...     

thanks moo, too bad such an appealing route had to die an early death though. 		 
 
 
 
    stratosphere
(Hive Bee)
03-09-04 20:26
No 493997
       maybe this method can bee revived with some...     

maybe this method can bee revived with some modification.

for instance by henry condensing phenyl-nitroethane with thioformaldehyde.
the only possible complication i see is that thioformaldehyde exists primarily as a trimer, i don't how that would effect the henry condensation.