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organic compounds
The structures of two compounds, (1D) (endo-endo-1,5,6,7,8,12,13,14,15,15- decachloropentacyclo[10.2.1.13,10.02,11.04,9]hexadeca-4(9),5,7-triene, C16H8Cl10), and (2D) (13,14-benzo-3,4,5,6-tetrachlorotetracyclo[6.4.2.29,12.02,7]hexadeca- 2(7),3,5-triene, C20H16Cl4) are reported. Both compounds are products of an irreversible dyotropic rearrangement where two H atoms are transferred intramolecularly onto a proximate π bond. These compounds are two members of several different series of compounds being studied with the aim of understanding the factors affecting the rate of this type of 2H group shift isomerization which can vary enormously with changes in the substitution pattern at, or near, the reaction zone. The atom-numbering system used for compounds of series (I) is that of Mackenzie, Proctor & Woodnutt [Tetrahedron (1987), 43, 5981–5993]. [The systematic name of (1D) using IUPAC nomenclature is endo-endo-3,4,5,6,10,11,12,13,16,16- decachloropentacyclo[6.6.1.13,6.02,7.09,14]hexadeca-9(14),10,12-triene].