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. 2019 Sep 16;9(50):29051–29055. doi: 10.1039/c9ra04609g

Optimization study of the rearrangement of 4a.


Entry	Iodine source	Solvent	Yield (%)
1	I₂ (2 equiv.)	DCM	Traces(60)^a
2	I₂ (2 equiv.)	THF	15(53)^a
3	I₂ (4 equiv.)	THF	54(31)^a
4	I₂ (6 equiv.)	THF	71
5	I₂ (8 equiv.)	THF	Traces
6	I₂ (6 equiv.)	THF	Traces^b
7	I₂ (6 equiv.)	THF	0^c
8	ICl (6 equiv.)	THF	0(90)^a
9	NIS (6 equiv.)	THF	Traces(60)^a
10	HI (6 equiv.)	THF	32(30)^a

^a

Isolated starting material.

^b

Reaction under argon.

^c

6 equiv. of water was added to the reaction : degradation.