Diallyldimethylsilane → [(Dimethylsilanediyl)di(propane-3,1-diyl)]bis(diphenylphosphane)

HRID 544514Notes

Reaction equation

HRID 544514 reaction equation
[CH3:1][Si:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[CH2:3][CH:4]=[CH2:5].[C:10]1([PH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:17]1([P:16]([CH2:5][CH2:4][CH2:3][Si:2]([CH2:6][CH2:7][CH2:8][P:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH3:9])[CH3:1])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 66190DiallyldimethylsilaneHCID 70017Diphenylphosphine2×

Product 1

HCID 53992545[(Dimethylsilanediyl)di(propane-3,1-diyl)]bis(diphenylphosphane)

Procedure

A mixture of 70 g (0.5 mole) dimethyl diallyl silane and 204.6 g (1.1 m mole, 10% excess over equivalent amounts) of diphenyl phosphine was reacted in the manner described in Example 1 at 40° C. The additionwas slow. After 24 hours, only about 10% of the diphenyl phosphine reacted.The irradiation of the reaction mixture was continued for a total of 160 hours. A subsequent fractional distillation provided 46 g of monoadduct, as a clear, slightly viscous liquid monoadduct of bp. 122°-134° C. at 0.05 mm and 113 g of the desired diadduct (Table 1) as a clear, light yellow, viscous liquid.

Workup

  1. customwas reacted in the manner
  2. customdescribed in Example 1 at 40° C
  3. customwas continued for a total of 160 hours
  4. distillationA subsequent fractional distillation
  5. customprovided 46 g of monoadduct

Sources & evidence

ORD record
ord-8b6c763885f9459fa0484106bfd98a00
Source dataset
uspto-grants-1984_05
Patent number
US04450299

Reaction notes

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