Toluene → 1-Pentene

HRID 463913Notes

Reaction equation

HRID 463913 reaction equation
C=C.[C:3]1(C)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>>[CH2:8]=[CH:3][CH2:4][CH2:5][CH3:6].[CH3:5]/[CH:4]=[CH:3]/[CH2:8][CH3:7]

Participants

4

Reactant 2

HCID 1140TolueneHCID 6325Ethylene

Product 2

HCID 80041-PenteneHCID 5326161trans-2-Pentene

Procedure

Addition of 1 atm. ethylene to a photostationary state mixture of IIa,b (1.4:1 a:b at 25°, toluene solution, see Example E) followed by continued photolysis at 25° resulted in slow production of free pentene, primarily trans-2-pentene. Less than 0.1 equiv pentene was evolved after 1 hour irradiation. Pentene formation did not occur thermally at 25°. The isomeric distribution, as measured after 15 and 60 min photolysis, was 85% trans-2-pentene, 10-12% cis-2-pentene, and 3-5% 1-pentene.

Workup

  1. additionto a photostationary state mixture of IIa,b (1.4:1 a:b at 25°
  2. customfollowed by continued photolysis at 25°

Sources & evidence

ORD record
ord-ea7108ca30564eb9b7d58b3dba4e8c64
Source dataset
uspto-grants-1985_10
Patent number
US04544789

Reaction notes

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