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https://doi.org/10.37358/Rev.Chim.1949

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Revista de Chimie (Rev. Chim.), Year 2015, Volume 66, Issue 7,





Mona Irina DOANA, Mariana-Gabriela DANILA, Constantin DRAGHICI, Petru FILIP
Reaction of Ketenes with Three Membered Heterocyclic Rings
IV. Addition of tert-butylcyanoketene to optically active styreneoxide and
1,1-diphenylethylenoxide

Abstract:

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 sC-C s 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. Keywords: cyanoketenes, TBCK, CCK, oxiranes


Issue: 2015, Volume 66, Issue 7
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