1003032-70-9Relevant academic research and scientific papers
A straightforward synthesis of alkenyl nonaflates from carbonyl compounds using nonafluorobutane-1-sulfonyl fluoride in combination with phosphazene bases
Vogel, Michael A. K.,Stark, Christian B. W.,Lyapkalo, Ilya M.
, p. 2907 - 2911 (2007)
An α-deprotonation of carbonyl compounds with phosphazene bases in the presence of the internal quenching reagent, nonafluorobutane-1-sulfonyl fluoride furnishes the corresponding alkenyl nonaflates. The new general method provides high yields of alkenyl nonaflates from aldehydes and cyclic ketones. However, it is not applicable to acyclic ketones whose nonaflate derivatives undergo fast E2 elimination to give alkynes. Successful synthesis of nonaflates from aldehydes requires carefully controlled reaction conditions to avoid the subsequent elimination to alkynes. A kinetic control enables high regioselectivities in favor of least substituted nonaflate regioisomers derived from cyclic ketones and modest Z-selectivities of alkenyl nonaflates derived from aldehydes. A new efficient protocol for highly selective removal of perfluorosulfolane admixture from technical nonafluorobutane-1-sulfonyl fluoride by basic hydrolysis is described. Georg Thieme Verlag Stuttgart.
