
TY  - JOUR
A1  - Clarke, DB 
A1  - Weavers, RT 
T1  - The Chemistry of Laurenene. XVI. Investigation of the Mechanism of a Cationic Rearrangement
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1993
VL  - 46
IS  - 8
SP  - 1163
EP  - 1175
KW  - 
UR  - https://doi.org/10.1071/CH9931163 
N2  - Some aspects of the mechanism of the acid-induced rearrangement of laurenan-2&#946;-ol have been deduced from deuterium- labelling studies. A key intermediate arises from two pathways, one involving a 1,4- and one a 1,5-hydride shift. Formation of this intermediate is partially suppressed by substitution of the migrating hydrogen by a deuterium. A proposed pathway which involves a 1,3-methyl migration has been disproved, and scrambling and loss of deuterium label has been accounted for in terms of equilibria involving lauren-1-ene and another previously reported rearrangement product. The rearrangement is strongly promoted in dichloromethane, and the product composition is highly solvent-dependent. 
ER  -

