Title of article :
Regioselective electrophilic addition vs epoxidation of mCPBA towards anti-Bredt olefin of fulleroid
Author/Authors :
Ikuma، نويسنده , , Naohiko and Sumioka، نويسنده , , Satoko and Asahara، نويسنده , , Haruyasu and Oshima، نويسنده , , Takumi، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2012
Abstract :
The mCPBA oxidation of methano-bridged [5,6] open fulleroid 1 anomalously resulted in the selective electrophilic addition at the bridgehead anti-Bredt double bond rather than the usual epoxidation. The mechanistic preference for the unprecedented stepwise addition of mCPBA vs the concerted epoxidation was explained in terms of the notable π-orbital misalignment (>30°) based on the B3LYP/6-31G(d) level calculation.
Keywords :
Fullerene , Anti-Bredt olefin , Electrophilic addition to olefin , Oxidation
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters
