Table 18.

Examples of the Schenck rearrangement.

Entry	Allylic isomer A	Allylic isomer B	Ref.
1	404a	404b	[424]
	At 40 °C in non-polar solvents, an approximately equimolar mixture of A and B is formed
2	405a	405b	[414]
	In hexane, A is rearranged to an equilibrium mixture of ~80% A and ~20% B
3	406a	406b	[425]
	At 60–70 °C in C6H6 or MeCN in the presence of TBHN or AIBN within 16–22 h, a 50:50 A:B mixture is formed
4	407a	407b	[426]
	In CCl4 at 40 °C for 141 h, the rearrangement proceeds by 80%
5	408a	408b	[427]
	In CDCl3, the rearrangement of A into B is completed in 24 h
6	409a	409b	[428]
	In CDCl3, the rearrangement is completed in 72 h
7	410a	410b	[429]
	In C6H6 in presence of 10 equiv TBHP and 20 mol % DTBN at 40 °C for 16 h, isomers A and B are formed in equal amounts
8	411a	411b	[430]
	In CDCl3 the rearrangement is completed in 48 h
9	412a	412b	[431]
	In CHCl3 for 5 d at room temperature, only partial conversion
10	413a	413b	[432]
	In CDCl3 the rearrangement is completed after 3–4 weeks; R: CO2H, CO2Me, CH2OH, CH3
11	414a	414b
	In CDCl3 the rearrangement is completed after 2–4 weeks; R: CO2H, CO2Me, CH2OH, CH3
12	415a	415b	[433]
	In CDCl3 the rearrangement is completed after 2 d
13	416a	416b	[434]
	In pyridine for 24 h, R: OH,CH3COO, F, Cl, conversion 12–58%
14	417a	417b	[435]
	In a 5 M solution of LiClO4 in Et2O the rearrangement is completed in 24 h
15	418a	418b	[436]
	In CDCl3/D2O, lyophilized PBS buffer at pH 7 for 20 h, the conversion is 14%
16	419a	419b	[136]
	In CH2Cl2 at −78 °C with BF3·OEt2 (1 mol %)
17	420a	420b	[437]
	In MeCN/H2O, only partial conversion.