Electroorganic Chemistry; 145:1Coupling Reaction of an Olefin with a Radical NO3 ·Generated by Anodic Oxidation of NO3 -

All articles of this category 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: H 2 O: Et 2 O = 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 . (1 S ,5 S )-(-)-ß-Pinene ( 13 ) is diastereoselectively transformed into (1 S ,2 R ,5 S )-(-)-myrtanol ( 14 ) by this technique.