Electroorganic chemistry; 145: Coupling reaction of an olefin with a radical NO.3 generated by anodic oxidation of NO-3

Article abstract of DOI:10.1055/s-1994-25594

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 NO^.₃ 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)-(-)-β-Pinene (13) is diastereoselectively transformed into (1S,2R,5S)-(-)-myrtanol (14) by this technique.