Table 3.

Oxidation of various substrates catalyzed by C1, C2 and C3 with a variety of oxidants.

Entry	Catalys t	Substrate	%Hydrox.a	%Desat.a
1	C1b,c	1,3-cyclohexadiene	< 1	8
2	C2c,d	1,3-cyclohexadiene	< 1	12
3	C3e	1,3-cyclohexadiene	< 1	11
4	C1f	1,4-cyclohexadiene	< 1	< 1
5	C2g	1,4-cyclohexadiene	< 1	< 1
6	C3e	1,4-cyclohexadiene	< 1	< 1
7	C1f	indoline	< 1	<1
8	C2g	indoline	< 1	< 1
9	C3e	indoline	<1	< 1
10	C1f	N-methyl indoline	< 1	20
11	C2g	N-methyl indoline	n/dh	n/dh
12	C3e	N-methyl indoline	< 1	16
13	C1f	[a,e]-dibenzohexamethyleneimine	< 1	< 1
14	C2g	[a,e]-dibenzohexamethyleneimine	< 1	6
15	C3e	[a,e]-dibenzohexamethyleneimine	n/dh	n/dh

^aReactions were run in CD₃CN to allow direct NMR analysis of products. Yields are reported relative to starting hydrocarbon and were determined by using 1,3,5-trimethylbenzene as internal standard added after the reaction. Control experiments with PhIO alone give no detectable products.

^b2 equiv. of tetrabutylammonium periodate used as primary oxidant, with no additives.

^cPeriodate was used to oxidize this substrate, as the product of reaction with iodosylbenzene, iodobenzene, interfered with the interpretation of the NMR spectrum of the product.

^d2 equiv. of tetrabutylammonium periodate used as primary oxidant, with 1 equiv. of NMO as additive.

^e2 equiv. of Oxone® (KHSO₅) used as primary oxidant, with no additives.

^f2 equiv. of PhIO used as primary oxidant, with no additives.

^g2 equiv. of Oxone® (KHSO₅) used as primary oxidant, with 1 equiv. of NMO as additive.

^hn/d indicates an unidentifiable product mixture.