
TY  - JOUR
A1  - Banwell, MG 
A1  - Ryan, JH 
A1  - Winkler, DA 
T1  - Carbocation-Mediated Rearrangements Within [n.m.1]Propellane Frameworks
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1991
VL  - 44
IS  - 4
SP  - 593
EP  - 611
KW  - 
UR  - https://doi.org/10.1071/CH9910593 
N2  - Mild thermolysis of the tetracyclic  mesylate (6) in the presence of traces of mineral acid afforded a mixture of the rearrangement products (21) and (22) as well the &#963;-anti- bishomotetralin (20). On treatment with methanesulfonic acid in dichloromethane, compound (20) gives rise to the [5.4.1] propellene (21) which, on prolonged exposure to these reaction conditions, isomerizes to the mesyloxymethyl compound (22). Under the same conditions, the &#963;-anti- bishomoindan (4) is converted into the [5.3.1] propellene (3) which, in turn, slowly rearranges to the [4.3.1] propellene (23). A mechanistic rationalization of these observations is advanced which also accounts for the formation of the novel by-product (16) observed during Simmons-Smith cyclopropanation of allylic alcohol (15a). 
ER  -

