1,2-migration in rhodium(II) carbene transfer reaction: remarkable steric effect on migratory aptitude.
A series of diazo carbonyl compounds bearing different substituents have been prepared in order to investigate the steric effect in 1,2-migration reaction of rhodium(II) carbene. Through the investigation on the diazo decomposition of these compounds with Rh2(OAc)4, it was found that the steric effect could dramatically influence the migratory aptitude. In many cases, the steric effect could override the inherent electronic effect of the substituent.
Xiao
Fengping
F
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Wang
Jianbo
J
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002855:Chromatography, Thin Layer; D004581:Electronics; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D012238:Rhodium / Q000737:chemistry*
D001391:Azo Compounds; D006838:Hydrocarbons; C030011:carbene; D012238:Rhodium; D008697:Methane