Reaction of 2-methylnaphthalene with hexachlorocyclopentadiene and structural characterization of a new addition-substitution product

Article abstract of DOI:10.1023/A:1021819518557

2-Methylnaphthalene undergoes Diels-Alder addition and substitution with hexachlorocyclopentadiene to give two products, 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-10- methyl-1,4;5,8-dimethanotriphenylene 1 and 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-10- (1′,2′,3′,4′,5′-pentachlorocyclopentadienyl) methyl-1, 4;5,8-dimethanotriphenylene 2. The molecular structure of 2 has been characterized by X-ray crystallography: C₂₆H₉Cl₁₇, monoclinic, space group P2₁/c, with a = 15.316(3), b = 13.698(3), c = 16.116(3) A, β = 96.113(3)°, and Z = 4.