C-C Bond Cleavage And Formation Of Cyclobutanols

Cyclobutanols are versatile intermediates in organic synthesis.They have many advantages,first of all,they are easily prepared by organometallic reagents and cyclobutanone.In addition,it's flexible that the ring-opening strategy of cyclobutanols can be realized via either radical-mediated cyclic C-C bond cleavage or transition-metalmediated ?-C elimination.At last,cyclobutanols come into being carbocation with the use of Lewis acid,which can be applied in the formation of C-C bond.Based on the advantages of cyclobutanols,the researches about efficient formation of 1-tetralones,polycyclic aromatic hydrocarbons(PAHs)and spiranes under mild conditions are described in this paper.The dissertation is composed of the following four parts.In part one,the recent progress on the transition-metal-mediated or radical-mediated C-C bond cleavage has been reviewed.In part two,a rapid synthesis of 1-tetralones via silver-catalyzed ring expansion of tertiary cyclobutanols is described.And the tandem radical-mediated cyclic C-C bond cleavage and intramolecular cyclization are involved.In part three,the synthesis of polycyclic aromatic hydrocarbons(PAHs)by iridium-catalyzed intermolecular cyclization between alkynes and ring-fused benzocyclobutenols(RBCBs)through C-C bond cleavage via ?-C elimination is described.In part four,the preliminary results about rapid synthesis of spiranes via the intramolecular cyclization between alkynes and carbocation generated by the interaction between alcohol and Lewis acid are described.