Divinyl sulfone → 1-tert-Butyl-4-{[2-(ethenesulfonyl)ethenyl]sulfanyl}benzene

HRID 437601Notes

Reaction equation

HRID 437601 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:13]([S:15]([CH:18]=[CH2:19])(=[O:17])=[O:16])=[CH2:14].C(N(CC)CC)C>C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH:14]=[CH:13][S:15]([CH:18]=[CH2:19])(=[O:17])=[O:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6496Divinyl sulfoneHCID 8471TriethylamineHCID 12801136p-t-Butylbenzenesulfenyl chloride

Product 1

HCID 545451191-tert-Butyl-4-{[2-(ethenesulfonyl)ethenyl]sulfanyl}benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a manner analogous to Example 1, 4-t-butylphenylsulfenyl chloride was added in 1:1 proportion to divinyl sulfone, subjected to treatment with triethylamine in benzene, and purified by column chromatography. The product, vinyl 2-(4-t-butylphenylthio)vinyl sulfone, was obtained as a brown oil which crystallized on standing, m.p. 62°-64° C; calculated for C14H18O2S2 :S, 22.7; found: S, 22.0; Cl, 0.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-0677209030c1412b9ad66da86dbb6f62
Source dataset
uspto-grants-1977_06
Patent number
US04031247

Reaction notes

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