
%0 Journal Article
%A Buckland, SJ 
%A Halton, B 
%A Stang, PJ 
%T Studies in the Cycloproparene Series: The Behavior of Alkylidenecycloproparenes Towards Nucleophiles and Oxidizing Agents
%J Australian Journal of Chemistry
%D 1988/06/01
%V 41
%N 6
%P 845-854
%K 
%R https://doi.org/10.1071/CH9880845
%U https://www.publish.csiro.au/paper/CH9880845 
%X The alkylidenecycloproparene (1) reacts with potassium t- butoxide to give the ring-expanded heptafulvene (3). Epoxidation of (1) provides the hydroxy  ketone (5) probably via the spiro  epoxide (4) but carbene additions fail to give spirocycle (7). Photooxygenation of (1a,b) gives products (5),(12)-(14) and (16) which are explicable in terms of initial formation of dioxetan (10); products (13) and (14) result from 1H-cyclopropa[b] naphthalenone (11). By comparison (1c) provides phenanthraquinone acetal (17) in low yield. With osmium tetroxide and sodium periodate , (1a) gives benzophenone (12a) in competition with hydroxy  ketone (5a) and 2,2-diphenylcyclobutanaphthalenone (20). The modes of formation of the various products are discussed. 
