Tetrahedron p. 8397 - 8406 (1996)
Update date:2022-08-16
Topics:
Freeman, Peter K.
Jang, Jung-Suk
Haugen, Christian M.
Irradiation of 3,4-dibromobiphenyl (BpBr2) in acetonitrile resulted in the formation of 4-bromobiphenyl (BpBr) and 3- bromobiphenyl (3-BpBr) in a ratio of 7.6 ± 0.1 up to 22% conversion of starting material. The dependence of the reciprocal of the quantum yield (1/Φ) upon 1/BpBr2 is linear. Reduction of BpBr2 with lithium di-tert-butylbiphenylide generates a 3.6:1.0 ratio of BpBr to 3-BpBr, while photohydrodebromination of BpBr2 in the presence of triethylamine produces a similar ratio of 1.8:1.0. Product determining radical stability was assessed by radical debromination of BpBr2 using Ph3SnH in THF, which resulted in a BpBr:3-BpBr ratio of 1.5:1.0 AMI calculations on the product determining radicals provide the basis for rationalization of products via excimer and radical anion intermediates.
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