Table 1.

Results of the insertion of 1 into aromatic disulfide bonds. The ratio of 1:10 determines the amount of [2]staffane formed.

Entry	Disulfide 10	R	Ratio of 1:10	Yield 6 [%]	Yield 11 [%]
1	10a	H	1:3	98a	–b
2	10a	H	1:1	51c	5c
3	10a	H	2:1	32c	10c
4	10a	H	3:1	33c	20c
5	10b	4-Cl	1:3	98a	–b
6	10b	4-Cl	2:1	34c	15c
7	10c	3,5-Cl2	1:3	96a	–b
8	10c	3,5-Cl2	2:1	34c	8c
9	10d	4-Me	1:3	96a	traces
10	10d	4-Me	2:1	35c	12c
11	10e	4-OMe	1:3	94a	traces
12	10f	2-Ph	1:3	61a	–b

^aIsolated yield, purified by column chromatography. ^bNot observed. ^cIsolated yield, purified by preparative TLC.