20534-58-1Relevant articles and documents
Formation of Alkyl Carbanions by Alkoxide Fragmentation in HMPT
Lomas, John S.,Dubois, Jacques-Emile
, p. 2067 - 2069 (1984)
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Kinetics of Ozonation. 6. Polycyclic Aliphatic Hydrocarbons.
Giamalva, David H.,Church, Daniel F.,Pryor, William A.
, p. 3429 - 3432 (2007/10/02)
The reaction of ozone with norbornane, adamantane and bicyclooctane has been studied, including kinetics and product studies as well as the determination of activation paprameters for the ozonation of norbornane.This work was carried out to distinguish between hydride abstraction and a concerted insertion mechanism for the ozonation of C-H bonds.Kinetically, norbornane behaves like a secondary hydrocarbon and lacks the rate acceleration expected if a carbocation intermediate were involved in a hydride abstraction mechanism.We interpret this and other results as supporting a 1,3-dipolar insertion mechanism for the reaction of ozone with C-H bonds.
MIGRATION APTITUDES OF CYCLIC AND POLYCYCLIC BRIDGEHEAD GROUPS IN THE CRIEGEE REARRANGEMENT
Wistuba, Eckehardt,Ruechardt, Christoph
, p. 3389 - 3392 (2007/10/02)
The migration aptitudes of cyclic and polycyclic bridgehead groups in the Criegee Rearrangement support ?-neighbouring group participation by pentacoordinated bonding and vertical charge stabilisation in the migrating group and therefore favour transition state 2b and not 2a.