
TY  - JOUR
A1  - O'Leary, MA 
A1  - Stringer, MB 
A1  - Wege, D 
T1  - Preparation of some substituted Bicyclo[4,2,0]octa-1,3,5-trienes (benzocyclobutenes)
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 9
SP  - 2003
EP  - 2012
KW  - 
UR  - https://doi.org/10.1071/CH9782003 
N2  - 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. 
ER  -

