roger2003 (Hive Bee)
12-17-03 12:47
No 477385
      Conversion of Nitrostyrene     

It is possible to convert Nitrostyrene to

Cinnamic acid
and
Phenylacetic acid
????

The Nitro Group in Organic Syntheses p. 163
(Conversion of Nitro Compunds into Cabocyclic Acids)

…a very efficient related reaction using a mixture of sodium nitrite and acetic acid in DMSO (at 30° C ; 6 h) has been reported. Because carbon-carbon double bonds and triple bonds and other various functional groups are compatible with this reaction conditions……

JOC 62, 234 (1997)

Will this yield cinnamic acid ?

roger2003
 
 
 
 
    roger2003
(Hive Bee)
12-19-03 14:10
No 477818
      JOC 62, 234 (1997)     

The JOC article was ref. before:

Post 447798 (Aurelius: "Ideas", Chemistry Discourse)

Anyone can post them ?

.
 
 
 
 
    Rhodium
(Chief Bee)
12-19-03 14:50
No 477828
      Nitro and Bromide to COOH
(Rated as: excellent)
    

Novel Transformation of Primary Nitroalkanes and Primary Alkyl Bromides to the Corresponding Carboxylic Acids
Matt, C.; Wagner, A.; Mioskowski, C.
J. Org. Chem. 62, 234-235 (1997) (../rhodium/pdf /nitro2bromide2acid.pdf)
DOI:10.1021/jo962110n



The Hive - Clandestine Chemists Without Borders
 
 
 
 
    roger2003
(Hive Bee)
12-20-03 08:23
No 477953
      (substituted) Phenylacetic acid     

1. Step

Knoevenagel Condensation of (substituted) Benzaldehyde and Nitromethan

Ber. 37, 4502 (1904)

2. Step
C=C double bond reduction

Post 426052 (Barium: "Novel high-yielding C=C reduction of nitrostyrenes", Novel Discourse)

3. Step

Transformation of Nitroalkanes to Phenylacetic Acids

J. Org. Chem. 62, 234-235 (1997)

roger2003