H, m, ArH); MS (70 eV) m/e (relative intensity), 190 (M+ 100), 192 (34); UV (EtOH) 286 nm.3-Bromo-,16b 3-bromo-5-chloro-,16b 3-chloro-,l6b 3,5-dichloro-,16a 3-fluoro,31 and 5-chloro-3-fluorobenzofuran were prepared by dehydrohalogenation of 1, 3, 10, 12, 29, and 31, respectively, with i-BuOK in Z-BuOH. The 5-chloro-3-fluoro derivative showed the following spectroscopic characteristics: NMR (CC14) 7.20-7.50 (3 H, m, ArH), 7.48 (1 H, d, 37HF = 4.5 Hz, 2-H); MS (70 eV), m/e (relative intensity) 170 (M+, 100), 172 (35); UV (EtOH) 287, 294 nm.

The major initial products of the self-reaction of α-tetralylperoxyls (C10H11O2•) in chlorobenzene at 303–353 K are equal concentrations of α-tetralol and α-tetralone in ~90% yield based on the number of initiating radicals. These yields are consistent with the non-radical (Russell) mechanism for self-reaction. Low concentrations of bis(α-tetralyl) peroxide are produced, indicating that there is a small but detectable free-radical contribution towards termination. C10H11O2• undergoes β-scission in this temperature range but steady-state concentrations of C10H11• are too low to influence the termination rate constant 2kt, or react with C10H11O2• to give (C10H11O2. α-Tetralol to α-tetralone ratios and total yields of these products are significantly less than 1 and 100%, respectively, in methanol and acetonitrile. Formaldehyde is produced in methanol indicating the involvement of α-hydroxymethylperoxyls, derived from the solvent, in termination. There is no evidence for a chain reaction or a zwitterion intermediate for self-reaction of C10H11O2• in solution.

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