java (Hive Addict)
09-23-04 20:06
No 532874
       Interesting method to Phenylnitroethanes     




..as read in "the Nitro Group in Organic Synthesis" page 127 the book is found here...

Post 532343 (java: "e-Book: THE NITRO GROUP ORGANIC SYNTHESIS", Chemistry Discourse)

Note: edited by java and corrected by rhodium, should read phenylnitroethanes
It is better to die on your feet than to live on your knees...Emiliano Zapata 		 
 
 
 
    Rhodium
(Chief Bee)
09-24-04 00:34
No 532907
       Questions     

Phenylnitropropenes? I can only see a synthesis of Phenylnitroethanes... How is Sulfonylnitromethane best prepared?
The Hive - Clandestine Chemists Without Borders 		 
 
 
 
    java
(Hive Addict)
09-24-04 08:17
No 532949
       Thinking Phenylnitropropene.........clarification     

In my wishful thinking I made an error , sorry about that, as for the arylsulfonylnitromethane synthesis , alI can gather it's a type of Merrifield resin bound nitroacetate and I wasn't able to locate a reference that may have something to do with their preparation.....java

An efficient procedure for the esterification of nitroacetic acid : application for the preparation of Merrifield Bound nitroacetate

J. Org. Chem. 46, 765, 1981

( not able to locate this reference)
It is better to die on your feet than to live on your knees...Emiliano Zapata 		 
 
 
 
    SpicyBrown
(Hive Bee)
09-24-04 23:34
No 533023
       J. Org. Chem. 46, 765, 1981 ...     

J. Org. Chem. 46, 765, 1981



-SpicyBrown 		 
 
 
 
    java
(Hive Addict)
09-25-04 03:04
No 533041
       Nitroethane from arylsulfonylnitromethane......     

Thank you SpicyBrown for the study , hence the synthesis of the arylsulfonylnitromethane is  found and also it seems that nitroethane  as well as  phenylnitroethane is made and the sulfonyl group is removed as per the original posting ..........java



It is better to die on your feet than to live on your knees...Emiliano Zapata 		 
 
 
 
    Nicodem
(Hive Bee)
09-25-04 21:17
No 533153
       Interconnecting threads     

I feel the need to connect this thread with the analogous one:
Post 475109 (Lego: "Amphetamines/PEAs w/o benzaldehyde or nitroethane", Novel Discourse)

The allkylation mechanism is the same, but removing the –COOMe group is way easier than –SO2Ph. Not to mention that alkyl nitroacetates are way more accessible (even by simply nitrating ethylacetoacetate!).
An interesting method otherwise and potentialy useful for those that have access to such reagents.
“The real drug-problem is that we need more and better drugs.” – J. Ott