Hexachlorocyclopentadiene → Chlordene

HRID 1741571Notes

Reaction equation

[Cl:1][C:2]1([Cl:11])[C:6]([Cl:7])=[C:5]([Cl:8])[C:4]([Cl:9])=[C:3]1[Cl:10].[CH:12]1[CH2:16][CH:15]=[CH:14][CH:13]=1>>[Cl:7][C:6]12[C:2]([Cl:11])([Cl:1])[C:3]([Cl:10])([C:4]([Cl:9])=[C:5]1[Cl:8])[CH:15]1[CH:16]2[CH:12]=[CH:13][CH2:14]1

Participants

Reactant 2

HCID 6478Hexachlorocyclopentadiene

HCID 7612Cyclopentadiene

Product 1

HCID 19519Chlordene

Procedure

In particular, the condensation reaction is a Dieis-Alder addition of hexachlorocyclopentadiene and cyclopentadiene to yield 4,5,6,7,8,8,-hexachloro-3a,4, 7,7a-tetrahydro-4,7-methanoindene which is oxidized with selenium dioxide to 1-exo-hydroxy-4,5,6,7,8,8-hexachloro-3a,4,7,7,a-tetrahydro-4,7-methanoindene. The composition of the heptachlor-hapten was verified by physical analysis.

Workup

customIn particular, the condensation reaction

Sources & evidence

ORD record: ord-efb7c93af5164faf8d9a3a73eb5abe76
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334528

Reaction notes

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