Some addition reactions of 1,2,3,4,7,7-hexachloronorborna-2,5-diene, 1,4,5,6,7,7-hexachloronorborn-5-en-2-one, and related compounds

The structures and stereochemistry have been elucidated of the products formed in the addition of methanol and of hydrogen to methyl 1,4,5,6,7,7-hexachloronorborna-2,5-diene-2-carboxylate; the epoxidation, the hydroboration–oxidation, and the addition of diazomethane to 1,2,3,4,7,7-hexachloronorborna-2,5-diene; and the lithium aluminium hydride reduction and the reaction of Grignard reagents with 1,4,5,6,7,7-hexachloronorborn-5-en-2-one. The results, when compared with published results of additions to 1,2,3,4,7,7-hexachloronorborna-2,5-diene and to 7,7-dimethylnorborn-2-ene, suggest that steric factors may not be entirely responsible for the direction of reagent attack.