Diphenylacetylene → HCID 4961564, compound

HRID 1033913Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH3:7])=[CH:5][P:4](C2C=CC=CC=2)[CH:3]=1.[C:14]1([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:7][C:6]1[C:2]2([CH3:1])[CH2:3][P:4]([C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:20]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 10390Diphenylacetylene

HCID 635827HCID 635827, compound

Product 1

HCID 4961564HCID 4961564, compound

Procedure

The starting compound 3,4-dimethyl-2,5,6-triphenyl-1-phosphanorbornadiene required for the preparation of NORBOS can be obtained according to the prior art in good yield in a two-stage synthesis. In the first process step, phenyldichlorophosphine or phenyldibromophosphine, or a mixture thereof, is reacted with dimethylbutadiene to give the 1-halo-2,5-dihydrophospholium salt, which is dehydrohalogenated by 2-methylpyridine to give 3,4-dimethyl-1-phenylphosphole. The reaction of the phosphole with diphenylacetylene in the second process step produce 3,4-dimethyl-2,5,6-triphenyl-1-phosphanorbornadiene.

Sources & evidence

ORD record: ord-5ac8b72044894406b26931b2e9e2353c
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312951

Reaction notes

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