Table 3.

Oxidation of (Z) and (E)-1,3,5-trimethoxy-2-[2-(4-methoxy-3-nitrobenzylsulfanyl)vinyl]benzene (11 and 12)

Entry	Compd	Oxidizing agent (eq.)	Solvent	Temp (°C)	Time (h)	Producta	Yieldb (%)
1	11	H2O2	AcOH	rt	8	—	—c
2	12	H2O2	AcOH	rt	24	16	40
3	11	H2O2	AcOH	5	6	13	55
4	12	H2O2	AcOH	5	6	14	75
5	12	H2O2	AcOH	60	6	16	85
6	11	m-CPBA (2.5)	MeOH	rt	12	—	—c
7	12	m-CPBA (2.5)	MeOH	rt	24	16	50
8	11	Oxonee (4)	THF/MeOH (2 : 1)	rt	24	13 & 15d	55
9	11	Oxonee (6)	THF/MeOH (2 : 1)	rt	24	15	65
10	11	H2O2	Hexafluoro-2-propanol	rt	2	13	40

^aStarting compound geometry was retained in the product.

^bYield of isolated product.

^cStarting compound decomposed.

^dPartial oxidation leading to mixture of sulfoxide and sulfone (ratio:15/85).

^eOxone was dissolved in water (2 mL g⁻¹) and then added to the reaction mixture.