Sulfur Dioxide → Sulfur trioxide

HRID 616654Notes

Reaction equation

HRID 616654 reaction equation
ClCC1C(CCl)=C(Cl)C(Cl)=C(Cl)C=1Cl.[S:15](=[O:17])=[O:16].[CH2:18]1[CH2:22][NH2+:21][CH2:20][CH2:19]1.[CH2:23]1[O:27][CH:26]2[O:28][CH:24]1[C:25]2([CH:40]([I:42])[I:41])[CH2:29][CH2:30][C:31]1([CH:37]([I:39])[I:38])[CH:35]2[O:36][CH:32]1[CH2:33][O:34]2>>[S:15](=[O:27])(=[O:17])=[O:16].[CH2:18]1[CH2:22][NH2+:21][CH2:20][CH2:19]1.[CH2:23]1[O:27][CH:26]2[O:28][CH:24]1[C:25]2([CH:40]([I:41])[I:42])[CH2:29][CH2:30][C:31]1([CH:37]([I:38])[I:39])[CH:35]2[O:36][CH:32]1[CH2:33][O:34]2

Participants

5

Reactant 3

HCID 1119Sulfur DioxideHCID 161932HCID 161932, compoundHCID 142514341,2,3,4-Tetrachloro-5,6-bis(chloromethyl)benzene

Product 2

HCID 24682Sulfur trioxideHCID 161932HCID 161932, compound

Procedure

The procedure of Example 3, when applied to 31.3 g of α,α',3,4,5,6-hexachloro-o-xylene, mp 92°-92.5° C, yielded an intensely purple solution but essentially no sulfur dioxide eveolution even during a refluxing period of 3 hours. The intermediate biradical was identified by its nuclear magnetic resonance peak at 4.65 ppm (present in about 8-10% abundance in the reaction mixture), whereas the dioxonium compound (90-92% of the reaction mixture) had the chemical shift of its protons at 6.31-6.33 ppm. After the stripping of the excess of sulfur trioxide, the dioxonium compound was obtained as a dark amber colored viscous oil in quantitative yield (63.5 g) and was further identified by its hydrolysis to three mole equivalents of sulfuric acid, two mole equivalents of hydrochloric acid and one mole equivalent of the cyclic sulfate of 3,4,5,6-tetrachloro-o-xylene-1,2-diol (see Example 32).

Workup

  1. customyielded an intensely purple solution

Sources & evidence

ORD record
ord-9b3b514a9b8b45028b8e25832e04023f
Source dataset
uspto-grants-1978_02
Patent number
US04075238

Reaction notes

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