A general synthesis of N-vinyl nitrones.
A general synthesis of a new type of heterodiene, the N-vinyl nitrone, is described. The synthetic sequence begins with the conjugate addition of benzeneselenol to nitroalkenes (in turn derived from Henry reaction of an aldehyde and a nitroalkane) to provide 2-selenenylnitroalkenes. These selenonitroalkanes are reduced to the corresponding hydroxylamines which are combined with aldehydes to form nitrones. The phenylselenenyl-containing nitrones are then oxidized to selenoxides which undergo syn-selenoxide elimination to provide N-vinyl nitrones. Three X-ray crystal structures of substituted N-vinyl nitrones were obtained. In addition, the first [4+2] cycloaddition of an N-vinyl nitrone is reported.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
Montgomery
Justin I
JI
D000475:Alkenes / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry; D018360:Crystallography, X-Ray; D004583:Electrons; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D012643:Selenium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D001555:Benzene Derivatives; D009589:Nitrogen Oxides; D016566:Organoselenium Compounds; C015388:nitrones; C018846:benzeneselenol; D012643:Selenium; D009584:Nitrogen; D010100:Oxygen