147287-37-4Relevant academic research and scientific papers
New Dienophiles and Dienes, III. On the Addition of Cyanoacetylene to Paracyclophane
Witulski, Bernhard,Ernst, Ludger,Hopf, Henning,Jones, Peter G.
, p. 2015 - 2022 (2007/10/02)
Heating a benzene solution of paracyclophane (2) in the presence of excess cyanoacetylene (1b) at 160 deg C in a sealed ampoule provides the novel 2:1-addition product 10, as well as the previously obtained cycloadducts 7-9.It is suggested that these Nenitzescu hydrocarbon systems are formed via the cyclobutadiene intermediates 17 and 18.This hypothesis is supported by the isolation of the side-products 1,2,4- and 1,2,3-tricyanobenzene (11 and 12).When a mixture of 7 and 8 is pyrolyzed at 220 deg C the novel dihydronaphthalene 24 is formed; the mechanism of this isomerization is discussed.The structures of 10 and 24 were confirmed by X-ray structure determination.
