AbstractN‐Allyl‐2‐methylaniline (12) forms on heating at 140° in xylene in the presence of zinc chloride 2‐allyl‐6‐methylanline (19) as major compound and 4‐allyl‐2‐methylaniline (20) as well as 2,7‐dimethyl‐indoline (21) as minor products. Compound21is also formed when19is heated in the presence of zinc chloride (scheme 2). That19arises from a charge‐induced [3s, 3s] sigmatropic rearrangement of12– and20from two consecutive [3s, 3s]‐sigmatropic transformations – follows from the reaction of N‐crotyl‐2‐methylaniline (13) in the presence of zinc chloride at 140°. 2‐(1′‐Methylallyl)‐6‐methylaniline (22) and 4‐crotyl‐2‐methylaniline (23) are formed exclusively. Small amounts of 2,3,7‐trimethyl‐indoline (24) and 2‐(cis‐ andtrans‐1′‐methyl‐propenyl)‐6‐methylaniline (cis‐ andtrans‐25) are observed as by‐products. Compound24arises from22in the presence of zinc chloride (scheme 3). Similar results are obtained when N‐allyl and N‐(2′‐methylallyl)‐N‐methyl‐aniline (14and15, respectively) are heated in the presence of zinc chloride. Whereas14gives nearly exclusively 2‐allyl‐N‐methyl‐aniline (28) and only small amounts of the corresponding 1, 2‐dimethyl‐indoline (29) and of 2‐(cis‐andtrans‐propenyl)‐N‐methyl‐aniline (cis‐andtrans‐27),15forms comparable amounts of 2‐(2′‐methylallyl)‐N‐methyl‐aniline (30), 1,2,2‐trimethyl‐indoline (31), and 2‐isobutenyl‐N‐methyl‐aniline (32) (scheme 4). Compound30, and also32, are transformed into31on heating in the presence of zinc chloride.Charge‐induced aromatic amino‐Claisenrearrangements are also observed when N‐allylated anilinium tetraphenylborates are heated at 100–105° in hexamethyl phosphoric acid triamide. Thus, N‐allyl‐ and N‐crotyl‐N, N‐dimethyl‐anilinium tetraphenylborate (16and17, respectively) yield 2‐allyl‐ and 2‐(1′‐methylallyl)‐N,N‐dimethyl‐aniline (33and34, respectively) besides small amounts of N, N‐dimethyl‐aniline. N‐Cinnamyl‐N, N‐dimethyl‐anilinium tetraphenylborate (18) gives, besides appreci