The photochemistry of 8-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene
- 1 July 1988
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 66 (7) , 1656-1662
- https://doi.org/10.1139/v88-269
Abstract
The direct irradiation of 6-cyanobenzocyclooctatetraene (7) led to 5- and 8-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (9 and 8), isolated in 21 and 63% yields, respectively. On triplet sensitized irradiation 8 gave 1- and 6-cyanobenzosemi-bullvalenes (4 and 12; Φ = 0.006 and 0.088, respectively) and naphthalene (Φ = 0.012). The direct irradiation of 8 yielded 12 (Φ = 0.050), naphthalene (Φ = 0.015), 7 (Φ = 0.007), 7-cyanobenzocyclooctatetraene (13; Φ = 0.007), and 5-cyano-7,8-benzotetracyclo[3.3.0.02,4.03,6]oct-7-ene (14; Φ = 0.004). Deuterium labelling studies suggest that 12 derives from Zimmerman di-π-methane rearrangement of 8, and that photoproduct cyclooctatetraene 7 is not formed by simple electrocyclic opening of the cyclobutene ring of 8.This publication has 0 references indexed in Scilit: