Cyclopentadiene → 2,3-Bis(trifluoromethyl)norbornadiene

Reaction equation

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

Participants

Reactant 2

HCID 7612Cyclopentadiene

HCID 69654Hexafluoro-2-butyne

Product 1

HCID 867359142,3-Bis(trifluoromethyl)norbornadiene

Procedure

Reaction of cyclopentadiene with hexafluorobut-2-yne at 100° C. for 24 hours gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptadiene which, upon hydrogenation over platinum, gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptane.

Sources & evidence

ORD record: ord-f8c20bdfa04a43f68ded73893e273afd
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220606

Reaction notes

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