Table 1. Intramolecular AAC of Allylic Azides^a.

entry	azide (R1, R2, R3, R4)	ter/int ratiob	triazole (yield, %)	dr (a/b)c
1	1 (H, H, H, H)	83:17	11 (72)
2	2 (Me, H, H, H)	67:33	12 (85)	1.7:1
3	3 (Ph, H, H, H)	84:16	13 (83)	1.4:1
4	4 (Ph, Me, H, H)12	64:36	14 (76)	1.3:1e
5	5 (Me, H, Et, H)	69:31	15 (93)	1.9:1
6	6 (Et, H, Me, H)	86:14	16 (88)	1.5:1
7	7 (Me, H, Ph, H)	81:19	17 (84)	2:1
8	8 (iPr, H, Ph, H)	74:26	18 (84)	1.5:1d
9	9 (H, H, H, Me)	88:12	19 (79)	1:1
10	10 (H, H, H, Ph)	74:26	20 (82)	1:1e

^aConditions: toluene, reflux, 1–2 h (except for entry 1: CHCl₃, reflux, 4 h).

^bEquilibrium ratio as determined by NMR analysis of purified allylic azides; compounds attained equilibrium over 1 week at room temperature.¹¹

^cRatio determined by NMR analysis of crude reaction mixtures.

^dThe relative stereochemistry of triazoles 18a and 18b was confirmed by X-ray crystallography (Supporting Information).

^eInseparable mixture.