A Nitro-Hunsdiecker Reaction: From Unsaturated Carboxylic Acids to Nitrostyrenes and Nitroarenes

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3055-3058

  Das, Jaya Prakash ^a   Sinha, Pradipta ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

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ARTICLE;

EID: 0442267252     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0262901     Document Type: Article

References (38)

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32. GC Monitoring for Nitrodecarboxylation of 4-Methoxycinnamic Acid 1. Nitric acid (21.35 M, 0.15 mL, 3 mM) was added to a stirred solution of 1 (178 mg, 1 mM) in MeCN (2 mL) at room temperature under an argon atmosphere. To this reaction mixture was added AIBN (3.3 mg, 2 mol %), and the mixture was stirred at 50 °C. An aliquot of 0.2 mL was taken out at different time intervals and quenched with ice-cold water (0.2 mL) followed by triethylamine (0.03 mL), and a known amount of β-nitrostyrene solution in chloroform (0.134 M) was added as a reference. The organic layer was separated and directly used for GC analysis. The yield of 4-methoxynitrostyrene 2 was found to be 75% after 4 h. It was also isolated by column chromatography in 68% yield.
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38. Typical Procedure. Nitric acid (21.35 M, 0.3 mL, 6 mM) was added to a stirred solution of α-phenylcinnamic acid 13 (448 mg, 2 mM) in MeCN (5 mL) at room temperature under an argon atmosphere followed by AIBN (7 mg, 0.042 mM), and the mixture was stirred at 50 °C. Upon completion (GC, TLC monitoring), ice-cold water (5 mL) was added and the product was extracted with diethyl ether (4 × 10 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, concentrated, and subjected to column chromatography (silicagel, eluent 19:1 v/v n-hexane/ethyl acetate) to afford (E)α-phenylnitrostyrene 14 (260 mg, 58%).