Mechanistic Analysis of Oxidative C-H Cleavages Using Inter- and Intramolecular Kinetic Isotope Effects.

Tetrahedron
Hyung Hoon Jung, Paul E Floreancig

Abstract

A series of monodeuterated benzylic and allylic ethers were subjected to oxidative carbon-hydrogen bond cleavage to determine the impact of structural variation on intramolecular kinetic isotope effects in DDQ-mediated cyclization reactions. These values are compared to the corresponding intermolecular kinetic isotope effects that were accessed through subjecting mixtures of non-deuterated and dideuterated substrates to the reaction conditions. The results indicate that carbon-hydrogen bond cleavage is rate determining and that a radical cation is most likely a key intermediate in the reaction mechanism.

References

Jun 28, 2007·The Journal of Organic Chemistry·Lori J Van OrdenScott D Rychnovsky
May 26, 2009·Reviews on Recent Clinical Trials·Louise P King, David Scott Miller

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Citations

Jul 12, 2012·The Journal of Organic Chemistry·Dane J Clausen, Paul E Floreancig
Nov 5, 2015·Angewandte Chemie·Alison E Wendlandt, Shannon S Stahl
Aug 11, 2010·Tetrahedron·Yubo CuiPaul E Floreancig
Jan 15, 2014·Organic Letters·Alexander J GrenningJohn A Porco
Jul 22, 2015·Organic Letters·GuangRong Peh, Paul E Floreancig
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Feb 18, 2012·Journal of the American Chemical Society·Esther BoessMartin Klussmann
May 20, 2017·Chemistry : a European Journal·Althea S-K TsangMatthew H Todd
Nov 15, 2018·Organic & Biomolecular Chemistry·Ali GouranourimiAlireza Ariafard
May 5, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nilesh ZawarePaul E Floreancig
Jun 22, 2019·Organic & Biomolecular Chemistry·Zdravko DŽambaski, Bojan P BondŽić
May 15, 2020·Journal of the American Chemical Society·Viktoria SteckRudi Fasan
Nov 15, 2017·Journal of the American Chemical Society·Cristian A Morales-RiveraPeng Liu
Mar 23, 2018·The Journal of Organic Chemistry·Jianyang DongQingmin Wang
Jun 13, 2018·The Journal of Organic Chemistry·Zhihua PengCuiyu Jiang

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