TY - JOUR
T1 - Anodic cyclization reactions
T2 - probing the chemistry of N,O-ketene acetal derived radical cations
AU - Huang, Yung tzung
AU - Moeller, Kevin D.
N1 - Funding Information:
We thank the National Science Foundation (CHE-9023698) 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 - 2006/7/3
Y1 - 2006/7/3
N2 - The chemical reactivity of radical cations derived from N,O-ketene acetals has been examined and compared with the reactivity of radical cations derived from both ketene dithioacetals and enol ethers. Synthetically, the N,O-ketene acetal radical cations lead to more efficient cyclization reactions than either the ketene dithioacetal or enol ether derived radical cations. Cyclic voltammetry experiments using allylsilane trapping groups show that the efficiency of these cyclizations is not due to the N,O-ketene acetal radical cations being more reactive but rather more stable to decomposition. Finally, cyclizations using chiral oxizolidinones were examined.
AB - The chemical reactivity of radical cations derived from N,O-ketene acetals has been examined and compared with the reactivity of radical cations derived from both ketene dithioacetals and enol ethers. Synthetically, the N,O-ketene acetal radical cations lead to more efficient cyclization reactions than either the ketene dithioacetal or enol ether derived radical cations. Cyclic voltammetry experiments using allylsilane trapping groups show that the efficiency of these cyclizations is not due to the N,O-ketene acetal radical cations being more reactive but rather more stable to decomposition. Finally, cyclizations using chiral oxizolidinones were examined.
KW - Anodic electrochemistry
KW - Ketene acetals
KW - Oxidative cyclizations
KW - Radical cations
UR - http://www.scopus.com/inward/record.url?scp=33646907468&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2006.04.009
DO - 10.1016/j.tet.2006.04.009
M3 - Article
AN - SCOPUS:33646907468
SN - 0040-4020
VL - 62
SP - 6536
EP - 6550
JO - Tetrahedron
JF - Tetrahedron
IS - 27
ER -