Phenylacetylene → 4-(phenylethynyl)phenylacetylene
Reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]#[C:16]C2C=CC(Br)=CC=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[Si](C#C)(C)C>>[C:1]1([C:7]#[C:8][C:12]2[CH:13]=[CH:14][C:9]([C:15]#[CH:16])=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
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 TBPA (supra) to yield 1,3,5,7-tetrakis[3′/4′-(phenylethynyl)phenyl]adamantane. Alternatively, phenylacetylene can be converted (B1) to 4-(phenylethynyl)phenylbromide that is subsequently reacted (C1) with trimethylsilylacetylene to form 4-(phenylethynyl)phenylacetylene. TBPA can then be reacted (with phenylethynylphenylacetylene to 1,3,5,7-tetrakis{3′/4′-[4″-(phenylethynyl)phenylethynyl]phenyl}-adarnantane. In a further extension reaction, phenylethynylphenylacetylene is reacted (2) with 1-bromo-4-iodobenzene to form 4-[4′-(phenylethynyl)phenylethynyl]phenylbromide that is further converted (C2) to 4-[4′-(phenylethynyl)phenylethynyl]acetylene. The so formed 4-[4′-(phenylethynyl)phenylethynyl]acetylene may then be reacted (A3) with TBA to yield 1,3,5,7-tetrakis-{3′/4′-[4″-(4′-(phenylethynyl)phenylethynyl)phenylethynyl]phenyl}adamantane.
Sources & evidence
- ORD record
- ord-d6faa901a73e429982d2e82d18798d1b
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07307137B2
Reaction notes
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