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

Citation
T. Shono et al., ELECTROORGANIC CHEMISTRY .145. COUPLING REACTION OF AN OLEFIN WITH A RADICAL NO3-CENTER-DOT GENERATED BY ANODIC-OXIDATION OF NO3-, Synthesis, (9), 1994, pp. 895-897
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00397881
Issue
9
Year of publication
1994
Pages
895 - 897
Database
ISI
SICI code
0039-7881(1994):9<895:EC.CRO>2.0.ZU;2-W
Abstract
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.