Phenylacetylene → Benzene, 1-ethynyl-2-(phenylethynyl)-
Reaction equation
[C:1]1(C#C)C=CC=C[CH:2]=1.[C:9]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10](Br)=[CH:11][CH:12]=[CH:13][CH:14]=1.C[Si](C#C)(C)C>>[C:9]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:1]#[CH:2]Participants
Procedure
In an especially contemplated arm extension strategy depicted in FIG. 4, in which AD represents an adamantane or diamantane group. Phenylacetylene is a starting molecule that is reacted (A1) with TBA (supra) to yield tetrakis(mono-tolanyl)-adamantane. Alternatively, phenylacetylene can be converted (B1) to tolanylbromide that is subsequently reacted (C1) with trimethylsilylacetylene to form tolanylacetylene. TBA can then be reacted (A2) with tolanylacetylene to tetrakis(bistolanyl )-adamantane. In a further extension reaction, tolanylacetylene is reacted (B2) with 1-bromo-4-iodobenzene to bistolanylbromide that is further converted (C2) to bistolanylacetylene. The so formed bistolanylacetylene may then be reacted (A3) with TBA to yield tetrakis(tristolanyl)-adamantane.
Sources & evidence
- ORD record
- ord-6774e58e9b5a4bc59ced7ad3912cdb2e
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06469123B1
Reaction notes
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