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Synthesis 1994; 1994(9): 895-897
DOI: 10.1055/s-1994-25594
short paper
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Electroorganic Chemistry; 145:1 Coupling Reaction of an Olefin with a Radical NO3 · Generated by Anodic Oxidation of NO3 -

Tatsuya Shono* , Mayuree Chuankamnerdkarn, Hirofumi Maekawa, Manabu Ishifune, Shigenori Kashimura
  • *Kinki University, 3-4-1 Kowakae, Higashi-Osaka 577, Japan
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Publication Date:
17 September 2002 (online)

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When NO- 3 is electrochemically oxidized in the presence of a variety of terminal and 1,2-disubstituted olefins 1 in a mixed solvent system (MeCN: H2O: Et2O = 10: 2:1), a radical NO3 is generated from NO- 3 and nitrate esters 3 are formed by a new coupling reaction of the olefin with the radical. The products 3 can be further transformed into the corresponding alcohols 4 and alkyl iodides 5. Under the same reaction conditions, 1,1-di- and 1,1,2-trisubstituted olefins 6 do not give nitrate esters but afford oxazoline derivatives 7. (1S,5S)-(-)-ß-Pinene (13) is diastereoselectively transformed into (1S,2R,5S)-(-)-myrtanol (14) by this technique.