
%0 Journal Article
%A O'Leary, MA 
%A Stringer, MB 
%A Wege, D 
%T Preparation of some substituted Bicyclo[4,2,0]octa-1,3,5-trienes (benzocyclobutenes)
%J Australian Journal of Chemistry
%D 1978/09/01
%V 31
%N 9
%P 2003-2012
%K 
%R https://doi.org/10.1071/CH9782003
%U https://www.publish.csiro.au/paper/CH9782003 
%X The reaction of benzyne (generated by the thermolysis of o- diazoniobenzoate) with the following alkenes has been examined: 1,1-dichloroethene (5) (vinylidene chloride), 1,1-dichloro-propene (7), 1,1-dichloro-2-methylpropene (17), 2-methylprop-1-en-1-yl acetate (18) and 2-chloro-prop-2-enenitrile (&#945;-chloroacrylonitrile) (22). Substituted bicyclo[4,2,0]octa-1,3,5-trienes resulting from 2+2 cycloaddition were obtained from (5), (7), and (22), while the reaction involving the en01 acetate (18) gave only 'ene' product, and that involving (17) gave an intractable mixture. (Z)- and (E)-1-Chloro-2-(o-chlorophenyl)propene were obtained as minor products in the reaction of benzyne with (7): these products result from a chlorine atom transfer to the aromatic ring, and a novel mechanism involving a diradical &#8594; carbene rearrangement is postulated. 
