61529-89-3Relevant academic research and scientific papers
Trimethylsilyl Cyanide - A Reagent for Umpolung, IX. Enol Esters of Acyl Cyanides: Syntheses and General Properties
Hertenstein, Ulrich,Huenig, Siegfried,Reichelt, Helmut,Schaller, Rainer
, p. 699 - 721 (2007/10/02)
According to Scheme 1 acyl cyanide-enol sulfonates 3-5, carboxylates 7-9, and phosphates 12 are synthesized on routes A-D in generally good yields.Judged by 13C NMR chemical shifts of C-3, the donor effect of the enol groups on the C=C bond decreases slightly in the order OP(O)(OEt)2 > OCO2Et > OCOCH3 > OCOCF3 > OSO2Me OSO2Ph > OSO2C4F9, but being always larger than the acceptor effect of the CN group.Reactions with nucleophiles to give 1,2-diketones (29, 30) and with radicals to form adducts 32 and 35 are described.Depending on the substituent pattern , and cycloadditions can be performed with 2f, 5f, and 12f.Different cyclopropanes 54 can be prepared from 5f.
