5-Vinyl-2-norbornene → Bicyclo(2.2.1)hept-2-ene, 5-ethyl-

HRID 1165283Notes

Reaction equation

HRID 1165283 reaction equation
[CH:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)=[CH2:2].C([Al](CC)CC)C>[Cl-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Ti+2]>[CH2:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)[CH3:2]

Participants

4

Reactant 2

HCID 182735-Vinyl-2-norborneneHCID 16682930Triethylaluminum

Product 1

HCID 85837Bicyclo(2.2.1)hept-2-ene, 5-ethyl-

Reagents, catalysts & solvents 1

HCID 124040768Titanocene dichiorideCatalyst

Procedure

The reaction was carried out in the same way as in Example 1 except that the substrate was changed to 5-vinylbicyclo[2. 2. 1]hept-2-ene, 6 mmol of titanocenedichloride and 60 mmol of triethyl aluminum were charged into the autoclave, and the reaction period was set to five hours, to produce 134.7 g of 5-ethylbicyclo[2. 2. 1]hept-2-ene having the purity of 98.9%. Analyses by proton NMR revealed that only the signal of unsaturated proton of norbornene could be noticed in the vicinity of 5.8 ppm (δ) whereas the signal of unsaturated proton of vinyl in the vicinity of 5.0 ppm (δ) could not be noticed.

Workup

  1. additionwere charged into the autoclave
  2. customthe reaction period

Sources & evidence

ORD record
ord-94828a4a448e4323b85812effae1f3cc
Source dataset
uspto-grants-1990_03
Patent number
US04908420

Reaction notes

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