Azobisisobutyronitrile → 9-Cyclopentyl-9-phosphabicyclo[3.3.1]nonane 9-cyclopentyl-9-phosphabicyclo[4.2.1]nonane

HRID 420831Notes

Reaction equation

[CH:1]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.N(C(C(C)C)C#N)=NC(C(C)C)C#N.[CH:23]1([PH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH:23]1([P:28]2[CH:5]3[CH2:6][CH2:7][CH2:8][CH:1]2[CH2:2][CH2:3][CH2:4]3)[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH:23]1([P:28]2[CH:6]3[CH2:7][CH2:8][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

A 25 ml stirred vessel was charged at room temperature under nitrogen with 2.0 g (18.5 mmol) of 1,5-cyclooctadiene (Aldrich, 82018 Taufkirchen, DE), 71 mg of azo-bis-isovaleronitrile (VAZO 67, Aldrich, 82018 Taufkirchen, DE) and 3.8 g of a 50% strength solution of monocyclopentylphosphine in toluene (Cytec). This initial charge was subsequently heated to a bath temperature of 80° C. with stirring. After 24 h it was cooled to room temperature, treated with a further 71 mg of AIBN and heated with stirring at a bath temperature of 80° C. for a further 24 h. Subsequently it was worked up by vacuum distillation, giving 2.3 g of cyclopentylphobane isomer mixture (60% of theory; b.p.: 95° C. at 0.05 mbar).

Workup

additionThis initial charge
stirringwith stirring
temperatureAfter 24 h it was cooled to room temperature
temperatureheated
stirringwith stirring at a bath temperature of 80° C. for a further 24 h
distillationSubsequently it was worked up by vacuum distillation
customgiving 2.3 g of cyclopentylphobane isomer mixture (60% of theory; b.p.: 95° C. at 0.05 mbar)

Sources & evidence

ORD record: ord-8a9efa35c8e34dfc84178de95c777e39
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097691B2

Reaction notes

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