| Abstract
| - The rearrangement of nitrones to lactams can be carried out by photochemical activation or bytreatment with Tf2O followed by KOH-promoted rearrangement (a modification of conditionsoriginally introduced by Barton). Substrates in which the nitrone is part of a fused bicyclic ringsystem have traditionally proven problematic for this kind of reaction. In this study, a series ofmono-, bi-, and tricyclic ring-fused nitrones were prepared to investigate the dependence of productson nitrone ring size and tether length. Results indicated that photochemical rearrangement ofnitrones in benzene afforded reasonably good yields (30−68%) of lactams, while the two-stepnonphotochemical process provided slightly better average yields (30−95%) of the same targets.
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