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Benzobicyclic azoxy compounds, used as thermal and photochemical precursors of isoindenes, are synthesized from 2,2-dialkyl-l,3-indandiones via a four-step sequence in which the key step is a sequential hydrolysis-oxidation procedure in which the use of a vibromixer is absolutely essential.

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7-Isopropyl-7-méthyl-5,6-diaza-2,3-benzobicyclo[2.2.1]hepta-2,5-diene 5-iV-Oxide (Id). The synthesis of azoxy Id from diester 7d involved essentially the same procedure as that used in making la. However, the oxidation was carried out with 90% H202. The purified product, a white powder, was isolated in 24% yield: mp 108-110 °C dec; NMR (CDC13) 0.75 (t, 6 H (on a Varían Model XL-100 spectrometer, this signal consists of two doublets)), 0.98-1.64 (m, 4 H, including a large singlet at 1.24), 5.08 (d, 1 ), 5.20-5.47 (m, 1 ), 7.05-7.67 (m, 4 H); IR (KBr) 3040 (w), 2975 (m), 2890 (w), 1515 (s), 1460 (s), 1365 (w), 775 (m), 730 (s), 710 (m) cm™1; exact mass (M+ -N20) caled for C13H16 172.1251, found 172.1252.

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