155619-06-0Relevant articles and documents
Acetolysis of 2-Aryl-1-methylpropyl Systems: Mechanism of the Formation of the Retained Product without Neighbouring Group Participation
Kinoshita, Tomomi,Takemoto, Masaki,Shibayama, Koichi,Takeuchi, Ken'ichi
, p. 2153 - 2174 (2007/10/02)
threo-2--1-(13C)methylpropyl p-bromobenzenesulphonate (threo-(13C)1-OBs) has been solvolyzed in acetic acid to give rise to the retained threo-1-OAc which contains a small amount of threo-(13C)1-OAc accompanying no 13C-scrambling.At 75percent conversion, the isomerized erythro-1-OBs has been obtained along with the unchanged threo-1-OBs.Also, the erythro-1-OTs has been found at 50percent conversion in the presence of NaOTs.These stereochemical results indicate strongly that the acetate with the retained configuration accompanying no 13C-scrambling is formed via isomerization of the substrate by inversive anion exchange and a successive ks pathway with configurational inversion.Such a retained product was not detected in the acetolysis of threo-1-methyl-2-phenylpropyltoluene-p-sulphonate with no electron withdrawing substituent.