1-Methyl-1,3-cyclopentadiene → HCID 178484295, compound

HRID 1613838Notes

Reaction equation

HRID 1613838 reaction equation
[CH3:1][N-:2][CH3:3].[CH3:4][N-:5][CH3:6].[CH3:7][N-:8][CH3:9].[CH3:10][N-]C.[Ti+4:13].C[C:15]1[CH2:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH3:1][N-:2][CH3:3].[CH3:4][N-:5][CH3:6].[CH3:7][N-:8][CH3:9].[CH3:10][Ti+3:13][CH:18]1[CH:17]=[CH:16][CH:15]=[CH:19]1

Participants

4

Reactant 2

HCID 667751-Methyl-1,3-cyclopentadieneHCID 123185Methanamine, N-methyl-, titanium(4+) salt (4:1)

Product 1

HCID 178484295HCID 178484295, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL Schlenk flask is charged with titanium tetrakis(dimethylamide), 3.73 g (16.64 mmole), and toluene, 100 mL. Methylcyclopentadiene, 5.33 g (66.54 mmole), is added to the magnetically stirred solution. The mixture is refluxed 1.5 hours. Solvent and volatiles are removed under vacuum leaving a brown residue. The residue is transferred to a microdistillation apparatus and a forerun of titanium tetrakis(dimethylamide) is distilled from the mixture (at 35°-40° C. and 0.025 mm Hg) followed by a red low melting solid (at 104°-108° C. and 0.025 mm Hg) which is determined to be methylcyclopentadienyltitanium tris(dimethylamide) by proton NMR.

Workup

  1. temperatureThe mixture is refluxed 1.5 hours
  2. customSolvent and volatiles are removed under vacuum
  3. customleaving a brown residue
  4. distillationa forerun of titanium tetrakis(dimethylamide) is distilled from the mixture (at 35°-40° C. and 0.025 mm Hg)
  5. customfollowed by a red low melting solid (at 104°-108° C. and 0.025 mm Hg) which

Sources & evidence

ORD record
ord-56cefdd766424a3db0d4394dde6d901b
Source dataset
uspto-grants-1993_03
Patent number
US05194532

Reaction notes

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