ELECTROORGANIC CHEMISTRY .145. COUPLING REACTION OF AN OLEFIN WITH A RADICAL NO3-CENTER-DOT GENERATED BY ANODIC-OXIDATION OF NO3-

When NO3- is electrochemically oxidized in the presence of a variety o f terminal and 1,2-disubstituted olefins 1 in a mixed solvent system ( MeCN:H2O:Et(2)O = 10:2: 1), a radical NO3. is generated from NO; and n itrate esters 3 are formed by a new coupling reaction of the olefin wi th the radical. The products 3 can be further transformed into the cor responding alcohols 4 and alkyl iodides 5. Under the same reaction con ditions, 1,1-di- and 1,1,2-trisubstituted olefins 6 do not give nitrat e esters but afford oxazolne derivatives 7. (1S,5S)-(-)-beta-Pinene (1 3) is diastereoselectively transformed into (1S,2R,5S)-( -)-myrtanol ( 14) by this technique.