The Vespiary

The Hive => Chemistry Discourse => Topic started by: java on September 23, 2004, 08:06:00 PM

Title: Interesting method to Phenylnitroethanes
Post by: java on September 23, 2004, 08:06:00 PM
( 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

Title: Questions
Post by: Rhodium on September 24, 2004, 12:34:00 AM
Phenylnitropropenes? I can only see a synthesis of Phenylnitroethanes... How is Sulfonylnitromethane best prepared?

Title: Thinking Phenylnitropropene.........clarification
Post by: java on September 24, 2004, 08:17:00 AM
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

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)

Title: J. Org. Chem. 46, 765, 1981 ...
Post by: SpicyBrown on September 24, 2004, 11:34:00 PM
J. Org. Chem. 46, 765, 1981


Title: Nitroethane from arylsulfonylnitromethane......
Post by: java on September 25, 2004, 03:04:00 AM
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


Title: Interconnecting threads
Post by: Nicodem on September 25, 2004, 09:17:00 PM
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.