Chlorination of 2,2,2,5-tetrachloro-6-methylbenzo[ d]-1,3,2-dioxaphosphole

An NMR investigation has shown that the reaction of 2,2,2,5-tetrachloro-6-methylbenzo[ d]-1,3,2-dioxaphosphole 2 with an excess of molecular chlorine occurs stepwise with high stereoselectivity to give 2,3,4,5,6,6-hexachloro-3-dichlorophosphoryl-5-methylcyclohex- 1-ene 4, which then undergoes stabil...

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Published inMendeleev communications Vol. 15; no. 5; pp. 181 - 183
Main Authors Varaksina, Elena N., Mironov, Vladimir F., Shtyrlina, Alfia A., Dobrynin, Alexey B., Litvinov, Igor A., Konovalov, Alexander I.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 2005
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Summary:An NMR investigation has shown that the reaction of 2,2,2,5-tetrachloro-6-methylbenzo[ d]-1,3,2-dioxaphosphole 2 with an excess of molecular chlorine occurs stepwise with high stereoselectivity to give 2,3,4,5,6,6-hexachloro-3-dichlorophosphoryl-5-methylcyclohex- 1-ene 4, which then undergoes stabilization via a 3,3-sigmatropic shift of the dichlorophosphonate fragment to give 1,2,4,4,5,6-hexachloro-3-dichlorophosphoryl-5-methylcyclohex-1-ene 5. The configuration of the hydrolysis product of the latter (1,2,4,4,5,6-hexachloro-5-methyl-3-phosphorylcyclohex-1-ene 6) was established by single crystal X-ray diffraction
ISSN:0959-9436
DOI:10.1070/MC2005v015n05ABEH002170