69703-96-4Relevant academic research and scientific papers
Diradical-promoted (n + 2 - 1) ring expansion: An efficient reaction for the synthesis of macrocyclic ketones
Rueedi, Georg,Oberli, Matthias A.,Nagel, Matthias,Hansen, Hans-Jurgen
, p. 3179 - 3181 (2007/10/03)
(Chemical Equation Presented) A diradical-promoted (n + 2 - 1) ring expansion reaction based on vinyl side chain insertion (+2C) and decarbonylation (-1C) has been developed. Flash vacuum pyrolysis (FVP) of medium- and large-ring 2-trimethylsilyloxy-2-vinyl-cycloalkanones at 500-600°C affords the one-carbon ring-expanded cycloalkanones in good yields. Methyl groups on the vinyl moiety are transformed regiospecifically as corresponding α- and β-substituents, respectively. 2-Ethynyl precursor analogues react in a manner similar to give α,β-unsaturated cyclic ketones.
