1,3-diiodo-2,2-dimethylpropane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chlorophenylacetonitrile (26.5 g), 1,3-diiodo-2,2-dimethylpropane (56 g) and dimethyl sulphoxide (300 ml) was added dropwise to a stirred suspension of powdered potassium hydroxide (40 g) in dry dimethylsulphoxide (300 ml). The mixture was stirred for one hour, then poured onto ice/water and extracted with ethyl acetate. The extracts yielded an oil which was distilled under vacuum to give 2,2-dimethyl-1-(2-chlorophenyl)cyclobutane carbonitrile, (b.p. 116°-120° C./1 mbar) which was recrystallised from petroleum ether (b.p. 60°-80° C.) m.p. 65°-69° C. poured onto ice/water extracted with ethyl acetate The extracts yielded an oil which was distilled under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenylacetonitrile (47.4 g) and 1,3-diiodo-2,2-dimethylpropane (131.2 g) was added dropwise over 2 hours at 25° C. to a stirred solution of powdered potassium hydroxide (90.7 g) in dry dimethylsulphoxide (600 ml) under a nitrogen atmosphere. The mixture was stirred overnight then poured onto water and extracted with ether (1000 ml). The extracts were decolourised with charcoal, filtered and concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum to give 2,2-dimethyl-1-phenylcyclobutane carbonitrile, (b.p. 101°-106° C./0.6mbar) as a pale yellow oil. then poured onto water extracted with ether (1000 ml) filtered concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenylacetonitrile (47.4 g) and 1,3-diiodo-2,2-dimethylpropane (131.2 g) was added dropwise over 2 hours at 25° C. to a stirred solution of powdered potassium hydroxide (90.7 g) in dry dimethylsulphoxide (600 ml) under a nitrogen atmosphere. The mixture was stirred overnight then poured onto water and extracted with ether (1000 ml). The extracts were decolourised with charcoal, filtered and concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum to give 2,2-dimethyl-1-phenylcyclobutane carbonitrile, (b.p. 101°-106° C./0.6mbar) as a pale yellow oil. then poured onto water extracted with ether (1000 ml) filtered concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chlorophenylacetonitrile (26.5 g), 1,3-diiodo-2,2-dimethylpropane (56 g) and dimethyl sulphoxide (300 ml) was added dropwise to a stirred suspension of powdered potassium hydroxide (40 g) in dry dimethylsulphoxide (300 ml). The mixture was stirred for one hour, then poured onto ice/water and extracted with ethyl acetate. The extracts yielded an oil which was distilled under vacuum to give 2,2-dimethyl-1-(2-chlorophenyl)cyclobutane carbonitrile, (b.p. 116°-120° C./1 mbar) which was recrystallised from petroleum ether (b.p. 60°-80° C.) m.p. 65°-69° C. poured onto ice/water extracted with ethyl acetate The extracts yielded an oil which was distilled under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenylacetonitrile (47.4 g) and 1,3-diiodo-2,2-dimethylpropane (131.2 g) was added dropwise over 2 hours at 25° C. to a stirred solution of powdered potassium hydroxide (90.7 g) in dry dimethylsulphoxide (600 ml) under a nitrogen atmosphere. The mixture was stirred overnight then poured onto water and extracted with ether (1000 ml). The extracts were decolourised with charcoal, filtered and concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum to give 2,2-dimethyl-1-phenylcyclobutane carbonitrile, (b.p. 101°-106° C./0.6mbar) as a pale yellow oil. then poured onto water extracted with ether (1000 ml) filtered concentrated in vacuo to yield an orange-brown oil which was distilled under vacuum