Chlorine → Chloroadamantylidene adamantane

HRID 247150

Reaction equation

HRID 247150 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[C:11]1[CH:18]3[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:20][CH:12]1[CH2:13]4)[CH2:17]3)[CH2:8]2.[Cl:21]Cl>ClC(Cl)(Cl)Cl>[Cl:21][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[C:2]1=[C:11]1[CH:12]3[CH2:20][CH:16]4[CH2:15][CH:14]([CH2:19][CH:18]1[CH2:17]4)[CH2:13]3)[CH2:10]2

Participants

4

Reactant 2

HCID 24526ChlorineHCID 141567Biadamantylidene

Product 1

HCID 12950367Chloroadamantylidene adamantane

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In Tetrahedron Letters 1970, 4579-82, J. H. Wieringa, J. Strating and H. Wynberg describe a process in which adamantylidene adamantane is reacted with chlorine is tetrachloromethane at a temperature of -20° to +10° C. to form 4-eq.-chloroadamantylidene adamantane in addition to polychlorinated products. The chloro-substituted adamantane compound is the starting point for further reaction in the presence of AgNO3 and THF/H2O to form a mixture of the corresponding 4-hydroxy-adamantylidene adamantane compounds, which with the appropriate oxidant (Jones reagent: CrO3, H2SO4, acetone) are finally converted into the corresponding ketone compound, in which the carbonyl group is in the 4-position.

Workup

  1. customat a temperature of -20° to +10° C.

Sources & evidence

ORD record
ord-7546b11291c740d58d0e845bb8155701
Source dataset
uspto-grants-1987_11
Patent number
US04705847

Linked notes

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