Sulfur Dioxide → Sulfur trioxide

HRID 1391278Notes

Reaction equation

HRID 1391278 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 evelution 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-d0ebdf68c63e4cc6acd960b38f6b0c8d
Source dataset
uspto-grants-1979_02
Patent number
US04141912

Reaction notes

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