Investigations into γ- vs. δ-selectivity.

Entrya	Product		γ : δb	ΔΔG‡c (kcal mol−1)	Yieldd
1		4k	—e	≤−1.77f	83
2		4l	>20 : 1	≤−1.77f	87
3		4m	—e	≤−1.77f	97
4		4n	—e	≤−1.77f	63
5		4o	11 : 1	−1.39	79
6		4p	13 : 1	−1.52	70
7		4q	2 : 1	−0.41	98g
8		7r	1 : 2	+0.38	84g
9h		10a	3 : 1	−0.69	57g
10h		10b	4 : 1	−0.82	67g

^aConditions A.

^bDetermined by ¹H or ¹⁹F NMR of crude mixture.

^cCalculated from experimental product ratios.

^dIsolated yield of depicted product.

^eδ-Chlorinated-isomer not detected.

^fCalculated assuming ≥20 : 1 ratio of 4 : 7.

^gIsolated as a mixture of γ- and δ-chlorinated isomers.

^hConditions: 1.0 equiv. N-chlorosulfamate 9, PhH (0.07 M), 2 blue Kessil lamps.¹¹