Azobisisobutyronitrile → HCID 58654521, compound

HRID 1351914Notes

Reaction equation

[P:1]([CH2:14][CH2:15][CH2:16][PH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([P:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:25]=[CH2:26].CC(N=NC(C#N)(C)C)(C#N)C>>[P:1]([CH2:14][CH2:15][CH2:16][P:17]([CH2:26][CH2:25][CH2:24][P:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 6547Azobisisobutyronitrile

HCID 15822375HCID 15822375, compound

HCID 16693666Diphenyl[3-(phenylphosphanyl)propyl]phosphane

Product 1

HCID 58654521HCID 58654521, compound

Conditions

Temperature: 210 °C

Procedure

Ph2P(CH2)3P(H)Ph (3.68 g, 10.9 mmol), allyldiethylphosphine (1.71 g, 13.1 mmol) and AIBN (0.011 g) were mixed in a Schlenk flask and radiated with a 365 nm UV lamp for 20 hours. After confirming that the reaction was complete by 31P NMR analysis, it was distilled under vacuum (<0.5 mm Hg) at a final heating mantle temperature of 210° C. for an hour to remove impurities. The ligand remained in the pot. Yield: 3.36 g (66%). 31P NMR (122 MHz, CDCl3, δ, ppm): −16.74 (s), −23.09 (s) and −25.98 (s). There are peaks near the three major peaks, which have not been determined if are part of the ligand or due to impurities. 1H NMR (500 MHz, CDCl3, δ, ppm): 1.001 (d of q, JH-P&H=7.0 Hz 4H's methylenes of ethyl groups), 1.3 to 2.2 (m, H's on methyls and propylenes) (d of t, JH-P&H=211 & 6.6 Hz, H on the P), and 7.30 to 7.47 (m, 15H's on phenyl rings).

Workup

distillationwas distilled under vacuum (<0.5 mm Hg) at
customto remove impurities

Sources & evidence

ORD record: ord-adcf19395f5a487c95a6370d14ba449e
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217848B2

Reaction notes

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