Author Topic: Conversion of Nitrostyrene  (Read 3198 times)

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roger2003

  • Guest
Conversion of Nitrostyrene
« on: December 17, 2003, 12:47:00 PM »
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

  • Guest
JOC 62, 234 (1997)
« Reply #1 on: December 19, 2003, 02:10:00 PM »
The JOC article was ref. before:

Post 447798

(Aurelius: "Ideas", Chemistry Discourse)


Anyone can post them ?


Rhodium

  • Guest
Nitro and Bromide to COOH
« Reply #2 on: December 19, 2003, 02:50:00 PM »
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)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/nitro2bromide2acid.pdf)
DOI:

10.1021/jo962110n






roger2003

  • Guest
(substituted) Phenylacetic acid
« Reply #3 on: December 20, 2003, 08:23:00 AM »
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)