Organohalogen compounds. Part II. The reactions of 2,3-dimethyl-buta-1,3-diene with chlorine and with iodine monochloride

doi:10.1039/P19720001986

Paper

Organohalogen compounds. Part II. The reactions of 2,3-dimethyl-buta-1,3-diene with chlorine and with iodine monochloride

Published 1972 · E. Z. Said, A. E. Tipping

Journal of The Chemical Society-perkin Transactions 1

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3

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0

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Abstract

The reaction of 2,3-dimethylbuta-1,3-diene with an equimolar amount of chlorine in carbon tetrachloride at –20 °C gives mainly trans-1,4-dichloro-2,3-dimethylbut-2-ene and 2-chloromethyl-3-methylbuta-1,3-diene. Chlorination in methylene chloride at –78 °C with gaseous chlorine yields initially a mixture of the same compounds and 1-chloro-2,3-dimethylbuta-1,3-diene in comparable amounts, together with the hydrogen chloride adducts 3-chloro-2,3-dimethylbut-1-ene and 1-chloro-2,3-dimethylbut-2-ene; further chlorination affords 1-chloro-3-chloromethyl-2-methylbuta-1,3-diene, 2,3-bis(chloromethyl)buta-1,3-diene, and 1,4-dichloro-2,3-bis(chloromethyl)but-2-ene and then a mixture of trichlorides, 1,2,3,4-tetrachloro-2-chloromethyl-3-methylbutane, and unidentified polychlorides. Bromination of trans-1,4-dichloro-2,3-dimethylbut-2-ene followed by dehydrobromination of the adduct gives 1,4-dichloro-2,3-dimethylbuta-1,3-diene in high yield. The reaction of 2,3-dimethyl-buta-1,3-diene with iodine monochloride affords, as the only identified product, 1,2,3,4-tetrachloro-2,3-dimethylbutane.

Study Snapshot

2,3-dimethyl-buta-1,3-diene reacts with chlorine to produce 1,2,3,4-tetrachloro-2,3-dimethylbutane, while iodine monochloride produces 1,2,3,4-tetrachloro-2,3-d

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Organohalogen compounds. Part II. The reactions of 2,3-dimethyl-buta-1,3-diene with chlorine and with iodine monochloride

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References

Citations

Electrophilic Additions to Dienes and Polyenes

Electrophilic additions to dienes and polyenes can be achieved using hydrogen, carbenium ions, halogens, sulfur, and selenium, and mercury.