Doana M.I.,Tostin nitzescu Organic Chemistry Center |
Danila M.-G.,Tostin nitzescu Organic Chemistry Center |
Draghici C.,Tostin nitzescu Organic Chemistry Center |
Filip P.,Tostin nitzescu Organic Chemistry Center
Revista de Chimie | Year: 2015
Addition of tert-butylcyanoketene to optically active styreneoxide and 1, 1-diphenyletyleneoxide are presented. Loss of optical activity during the addition reaction of TBCK to optically active styrene oxide (R (-)) proves that the process is a stepwise one involving an open intermediate allowing free rotation around the ∞C-Cs bond adjacent to the aromatic ring. The identified products for the addition of TBCK to 1, 1-diphenyletyleneoxide are two isomeric acetals and an unsaturated ester. All structure attributions are based on IR, 1H and 13C NMR and MS data.