TY - JOUR
T1 - Anodic oxidations and polarity
T2 - exploring the chemistry of olefinic radical cations
AU - Tang, Feili
AU - Moeller, Kevin D.
N1 - Funding Information:
We thank the National Science Foundation (CHE-0809142) for their generous support of our work. We also gratefully acknowledge the Washington University High Resolution NMR facility, partially supported by NIH grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIHRR00954, for their assistance.
PY - 2009/12/26
Y1 - 2009/12/26
N2 - The cyclization chemistry of radical cations derived from electron-rich olefins has been examined and the relationship between the polarization of the radical cation and the chemoselectivity of the reaction probed. It was found that more polarized radical cations favor carbon-carbon bond formation while less polarized radical cations favor carbon-heteroatom bond formation. A new approach to the synthesis of quaternary carbons was uncovered and the compatibility of ene diol ethers with anodic olefin coupling reactions examined.
AB - The cyclization chemistry of radical cations derived from electron-rich olefins has been examined and the relationship between the polarization of the radical cation and the chemoselectivity of the reaction probed. It was found that more polarized radical cations favor carbon-carbon bond formation while less polarized radical cations favor carbon-heteroatom bond formation. A new approach to the synthesis of quaternary carbons was uncovered and the compatibility of ene diol ethers with anodic olefin coupling reactions examined.
UR - http://www.scopus.com/inward/record.url?scp=70449702206&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2009.09.028
DO - 10.1016/j.tet.2009.09.028
M3 - Article
AN - SCOPUS:70449702206
SN - 0040-4020
VL - 65
SP - 10863
EP - 10875
JO - Tetrahedron
JF - Tetrahedron
IS - 52
ER -