Triphenylphosphine → HCID 86760815, compound

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][CH:7]1[C:11](=C)[CH2:10][CH2:9][C:8]1([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14].[O:28]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:24][C:22]([F:23])([F:25])[C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([C:2]([F:26])([F:27])[F:1])[CH:21]=1)[CH2:6][CH:7]1[C:11](=[O:28])[CH2:10][CH2:9][C:8]1([CH:16]([CH3:18])[CH3:17])[C:13]([NH2:15])=[O:14]

Participants

Procedure

A solution of 3,5-bis(trifluoromethyl)benzyl 3-methylene-1-isopropylcyclopentane-carboxamide (910 mg, 2.31 mmol) in dichloromethane (50 mL) was cooled to −78° C. and a stream of ozone was passed through until the permanent blue color indicated complete consumption of the olefin. The excess ozone was purged with a stream of nitrogen, and triphenylphosphine (729 mg, 2.78 mmol) was added. The cooling bath was removed, and the reaction mixture was allowed to stir at ambient temperature overnight. The solvent was removed in vacuo, the residue was purified by column chromatography (silica gel, ethyl acetate:hexane/1:2) to give 760.7 mg (83%) of the desired product. 1H NMR (500 MHz, CDCl3): 7.81 (s, 1H), 7.74 (s, 2H), 6.16 (bs, 1H), 6.61 (m, 2H), 2.78 (bd, J=18.07 Hz, 1H), 2.40 to 2.20 (bm, 4H), 2.08-1.98 (m, 2H), 0.99 (d, J=6.86 Hz, 3H), 0.97 (d, J=6.87 Hz, 3H).