Methane, tris(methylthio)- → 1-Tris(methylthio)methyl acenaphthene

HRID 2051511Notes

Reaction equation

HRID 2051511 reaction equation
[CH3:1][S:2][CH:3]([S:6][CH3:7])[S:4][CH3:5].[Li]CCCC.Br[CH:14]1[C:24]2=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]2)[CH:19]=[CH:18][CH:17]=[C:16]3[CH2:15]1>C1COCC1.CCCCCC>[CH3:1][S:2][C:3]([S:6][CH3:7])([S:4][CH3:5])[CH:15]1[C:16]2=[C:25]3[C:20](=[CH:19][CH:18]=[CH:17]2)[CH:21]=[CH:22][CH:23]=[C:24]3[CH2:14]1

Participants

6

Reactant 3

HCID 138491Methane, tris(methylthio)-HCID 136344461-Bromo-acenaphtheneHCID 178418339Butyllithium

Product 1

HCID 147997751-Tris(methylthio)methyl acenaphthene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Tris(methylthio)methane (22 g) was dissolved in THF (100 ml) under N2 at -78° C. 1.6 M BuLi in hexane solution (95 ml) was added slowly to yield a dense white precipitate. 1-Bromoacenaphthene (31.4 g) was dissolved in 20 ml of dry THF and added slowly to the above suspension to yield, after 10 minutes, a colorless solution. This was allowed to warm to room temperature, with the development of a brown color, and stirred overnight.

Workup

  1. customto yield a dense white precipitate
  2. additionadded slowly to the above suspension
  3. customto yield, after 10 minutes

Sources & evidence

ORD record
ord-f28358ec98a54078811d6cbfe947f216
Source dataset
uspto-grants-1991_05
Patent number
US05019588

Reaction notes

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