Azobisisobutyronitrile → HCID 13718277, compound

HRID 851450Notes

Reaction equation

HRID 851450 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:19]1([PH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[O:5]=[C:4]1[CH2:3][CH:2]([CH2:1][P:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:6]1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 12661DiketeneHCID 70017Diphenylphosphine

Product 1

HCID 13718277HCID 13718277, compound

Conditions

Temperature
85 °C

Procedure

A mixture of 2.1 parts of diketene and 0.4 parts of azobisisobutyronitrile were added dropwise over 15 minutes to 18.6 parts of diphenylphosphine which was stirred and heated at 85° C. in a nitrogen atmosphere. After the addition, the reaction mixture was heated for a further 5 minutes at 85° C., then cooled to room temperature. The excess diphenylphosphine and volatile impurities were removed by distillation on a wiped wall still at a wall temperature of 85° C. and a pressure of 0.04 mb, then the residue was distilled in the wiped wall still at 120° C. and a pressure of 0.013 mb. The product, (2-oxo-4-oxetanylmethyl)-diphenylphosphine, was obtained as a colourless oil and had an absorption at 1825 cm-1 in the infra-red spectrum, characteristic of a β-lactone.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated for a further 5 minutes at 85° C.
  3. temperaturecooled to room temperature
  4. customThe excess diphenylphosphine and volatile impurities were removed by distillation on a wiped wall still at a wall temperature of 85° C.
  5. distillationa pressure of 0.04 mb, then the residue was distilled in the wiped wall still at 120° C.

Sources & evidence

ORD record
ord-0c787edf61c0464083d055de98fde3ab
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

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