
%0 Journal Article
%A Banwell, MG 
%A Ryan, JH 
%A Winkler, DA 
%T Carbocation-Mediated Rearrangements Within [n.m.1]Propellane Frameworks
%J Australian Journal of Chemistry
%D 1991/04/01
%V 44
%N 4
%P 593-611
%K 
%R https://doi.org/10.1071/CH9910593
%U https://www.publish.csiro.au/paper/CH9910593 
%X 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). 
