87874-53-1Relevant academic research and scientific papers
COMPETITION OF REDUCTIVE DEHALOGENATION, ABSTRACTION-ADDITION, AND FAVORSKII REARRANGEMENT IN THE REACTION OF α-BROMOCYCLOPROPYL KETONES WITH SODIUM ALCOHOLATES
Kulinkovich, O. G.,Tishchenko, I. G.,Sviridov, S. V.
, p. 1275 - 1280 (2007/10/02)
Oxidation of the corresponding α-bromocyclopropylcarbinols gave 7-exo-bromo-7-endo-benzoylbicycloheptane, E-1-bromo-1-benzoyl-2-phenylcyclopropane, E-1-bromo-1-benzoyl-2-butylcyclopropane, E-1-bromo-1-acetyl-2-phenylcyclopropane, and 7-exo-bromo-7-endo-acetylbicycloheptane and the reactions of these compounds with sodium alcoholates were studied.Depending on the structure of the starting α-bromocyclopropyl ketone, the alcoholate used, and the solvent, the predominant reaction is reductive dehalogenation, Favorskii rearrangement or abstraction-addition.In the latter case, 2-alkoxycyclopropyl ketone intermediates are isomerized to 4,5-dihydrofuran derivatives.
