Abstract
| - A continued study of the recently discovered diazotizative allylation (DiazAll) reaction of anilinederivatives is reported. Several allyl reagents, commonly used in radical allylation reactions, wereevaluated, and some of these reagents resulted in allylation when used in the DiazAll reaction.The best result was obtained with allyl bromide. Substituted allylic bromides gave the correspondingallyl aromatic compounds in poor to excellent yields. In comparison with an established methodfor aromatic allylation, the DiazAll reaction performed well and was superior when a more complexallylic bromide was used. Finally, a new allylation−bromocyclization reaction was demonstratedand used in the synthesis of a known inhibitor of phenylethanolamine N-methyltransferase (PNMT),an enzyme involved in the biosynthesis of adrenaline.
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