Trifluoroacetic acid → HCID 20131150, compound

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:12]O2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(=[S:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:12][S:32]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Procedure

To a stirred solution of 2-(3-phenylpropyl)oxirane (Example 35b) (2.0 g, 0.0123 mol) and triphenylphosphine sulphide (3.62 g, 0.0123 mol) in toluene (20 ml), trifluoroacetic acid (1.40 g, 0.0123 mol) was added over 5 min. After stirring for 1 hour at room temperature, the reaction mixture was washed with water, sodium hydrogen carbonate solution and again with water. After drying (MgSO4) and removal of solvent at reduced pressure, the product contaminated with triphenylphosphine oxide was isolated as a crystalline mass. Attempted purification of the thiirane resulted in its extensive decomposition and it was therefore used in its crude state.