Abstract
Aldehydes and ketones are easily converted to their corresponding gem-dichlorides using a mixture of chlorodiphenylphosphine and N-chlorosuccinimide (ClPPh2/NCS) in dichloromethane under neutral conditions and at room temperature.
ACKNOWLEDGMENT
We gratefully acknowledge the support of this work by Damghan University of the Basic Sciences Research Council.
Notes
a Molar ratio is related to aldehyde/tertiary phosphine/NCS.
b This reaction was carried out in acetonitrile as solvent.
a Molar ratio is related to aldehyde or ketone/ClPPh2/NCS.
b Isolated yields.
c In this case, equimolar amounts of the related gem-dichloride 10 and 1-(1-chloroethenyl)-4-nitrobenzene 13 were obtained on the basis of NMR analysis.
d Bp 71–72°C (4 mm) (lit.[15] 71°C, 4 mm).
e NBS was used instead of NCS in this case.
f A mixture of dibromomethylbenzene 12 and bromochloromethylbenzene 14 was produced in a 4:1 ratio together with a trace amount of dichloromethylbenzene 7 in this case.