Cyclotetrasilane, octaethyl- → HCID 22918068, compound

HRID 1376941Notes

Reaction equation

HRID 1376941 reaction equation
[CH2:1]([Si:3]1([CH2:19][CH3:20])[Si:6]([CH2:9][CH3:10])([CH2:7][CH3:8])[Si:5]([CH2:13][CH3:14])([CH2:11][CH3:12])[Si:4]1([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:2].[C:21]1([Si:27]([Li])([CH3:29])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:9]([Si:6]([CH2:7][CH3:8])([Si:3]([CH2:1][CH3:2])([CH2:19][CH3:20])[Si:4]([CH2:15][CH3:16])([CH2:17][CH3:18])[Si:5]([CH2:13][CH3:14])([CH2:11][CH3:12])[Si:27]([CH3:29])([CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[Si:27]([CH3:29])([CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:10]

Participants

4

Reactant 2

HCID 529608Cyclotetrasilane, octaethyl-HCID 178506967HCID 178506967, compound

Product 1

HCID 22918068HCID 22918068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In an argon atmosphere, to a tetrahydrofuran solution (1 ml) of 68 mg (0.20 mmol) of octaethylcyclotetrasilane was added 0.72 ml (0.20 mmol) of a tetrahydrofuran solution (0.26M) of phenyldimethylsilyllithium, and stirred at 0° C. for 15 minutes. Then, tetrahydrofuran was distilled out under vacuum, and hexane (1 ml) was added to afford a hexane solution (Solution 1). A dichloromethane solution (1 ml) of 31 mg (0.05 mmol) of 2,2,3,3,4,4,5,5-octaethyl-1,1,6,6-tetramethyl-1,6-diphenylhexasilane (1) obtained in Example 1 was treated with 15 mg (0.10 mmol) of trifluoromethanesulfonic acid at room temperature for 30 minutes to give 1,6-bis(trifluoromethanesulfonyloxy) hexasilanes. Then, dichloromethane was distilled out under vacuum, and hexane (1 ml) was added to give a hexane solution (Solution 2). The Solution 1 was added to the Solution 2 at -78° C. and stirred for 15 minutes. Methanol (0.1 ml) and triethylamine (0.1 ml) were added, then saturated aqueous sodium bicarbonate solution (2 ml) was added, stirred, the hexane layer was separated, and dried with magnesium sulfate. The resulting crude product was purified by a silica gel column (hexane) chromatography to afford 43 mg (61% yield) of hexadecasilane (6).

Workup

  1. distillationThen, tetrahydrofuran was distilled out under vacuum, and hexane (1 ml)
  2. additionwas added

Sources & evidence

ORD record
ord-bb88b4615fdb416f94775bdb29399dfa
Source dataset
uspto-grants-1997_09
Patent number
US05663271

Reaction notes

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