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
Pages
4
From page
3581
To page
3584
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
Serial Year
2012
Journal title
Tetrahedron Letters
Record number
1881156
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