Dichloromethane → 1-(4-Formylphenyl)cyclopropane-1-carbonitrile

Reaction equation

[O:1]=[O+][O-].[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=C.C(Cl)Cl>>[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:1]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 24823Ozone

HCID 666626411-(4-Vinylphenyl)cyclopropanecarbonitrile

Product 1

HCID 866022841-(4-Formylphenyl)cyclopropane-1-carbonitrile

Procedure

Ozone was bubbled through a solution of 1-(4-vinylphenyl)cyclopropanecarbonitrile (1.8 g, 0.011 mol) in methylene chloride (40 mL, 0.6 mol) at −78° C. until a blue color appeared and then nitrogen was bubbled through the solution for 10 minutes. Methyl sulfide was added and the mixture was stirred overnight. The mixture was washed with water and brine successively, dried, and concentrated to give the desired product.