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

反応式

[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]

参加物

反応物 3

HCID 6344Dichloromethane

HCID 24823Ozone

HCID 666626411-(4-Vinylphenyl)cyclopropanecarbonitrile

生成物 1

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

実験手順

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.