Triphenylphosphine → Tetradec-7-ene

HRID 1678946Notes

Reaction equation

HRID 1678946 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Sn](CCCC)(CCCC)CCCC)CCC>[W](Cl)(Cl)(Cl)(Cl)(Cl)Cl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 15098TetrabutyltinHCID 25209Tetradec-7-ene2×HCID 521661CID 5216612×

Product 3

HCID 25209Tetradec-7-eneHCID 520743Hexadec-7-eneHCID 521661CID 521661

Reagents, catalysts & solvents 1

HCID 83301Tungsten hexachlorideCatalyst

Procedure

7-Tetradecene and 9-octadecene were cross-metathesized employing a homogeneous modified catalyst. For the reaction, 1 mole 7-tetradecene and 1 mole 9-octadecene were combined in the reactor with 13 millimoles tungsten hexachloride. Triphenylphosphine (6.5 millimoles) was then charged to the reactor followed by the addition of 13 millimoles tetrabutyl tin. The reaction was conducted at 115° C and after 330 minutes reaction, near equilibrium conversion of the olefins was obtained with high selectivity to the equilibrium mixture of 1-part 7-tetradecene, 1 part 9-octadecene and 2 parts 7-hexadecene. When the experiment was repeated in an identical manner but using an unmodified catalyst (13 millimoles tungsten hexachloride with 13 millimoles tetrabutyl tin) conversion of the olefins was significantly greater than the theoretical equilibrium conversion due to the lower selectivity of the reaction to the desired cross-metathesized products.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-fd439f1193024e988016522ffcf11a14
Source dataset
uspto-grants-1978_03
Patent number
US04078012

Reaction notes

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