89697-38-1Relevant academic research and scientific papers
Addition of organomagnesium reagents to ring epoxy-ketones. III. 2,3-Epoxycyclohexanone
Sepulveda, Jose,Soriano, Concepcion,Mestres, Ramon,Sendra, Jose
, p. 240 - 244 (2007/10/02)
The addition of ethyl-(-70 deg C), vinyl-(11 deg C) and ethynylmagnesium (20 deg C) bromides to 2,3-epoxycyclohexanone 1 gave mixtures of the cis-trans epoxycyclohexanols 2-4, and some derived adducts 5-8, in relative amounts depending on the Grignard reagent used, temperature and reaction time.The epoxyalcohols were isolated from short time reactin mixtures whereas the epoxide ring opening adducts were better obtained from longer reaction times and higher temperatures.Bromodiols 5-7 derive from the cis primary adducts 2a-4a and epoxyalcohol 8 from the trans ethyl epoxy-alkoxide conjugate of 2b.Configurations could be assigned through combined chemical and spectroscopical evidence, but for the elucidation of the structures of the divinyl diols 9 and 10 double resonance and INDOR techniques were necessary.
