Cyclopentadiene → 2,3-Difluoro-2,3-bis(trifluoromethyl) bicyclo[2.2.1] heptane

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]([F:10])=[C:4]([F:9])[C:5]([F:8])([F:7])[F:6].[CH:13]1[CH2:17][CH:16]=[CH:15][CH:14]=1>>[F:9][C:4]1([C:5]([F:8])([F:7])[F:6])[C:3]([F:10])([C:2]([F:11])([F:12])[F:1])[CH:16]2[CH2:17][CH:13]1[CH2:14][CH2:15]2

Participants

Reactant 2

HCID 7612Cyclopentadiene

HCID 96781,1,1,2,3,4,4,4-Octafluorobut-2-ene

Product 1

HCID 570670552,3-Difluoro-2,3-bis(trifluoromethyl) bicyclo[2.2.1] heptane

Procedure

In a like manner, octafluoro-but-2-ene and cyclopentadiene react to give 2,3-difluoro-2,3-bis(trifluoromethyl) bicyclo [2.2.1] heptane which, after hydrogenation over ruthenium gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptane.

Sources & evidence

ORD record: ord-d7c80e26912c4f81ad5164f4f4e35f18
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220606

Reaction notes

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