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Polyhalogenated Bicycloocta-1,5,7-trienes, X. - Aromatizing Nucleophilic Substitutions and Rearrangements of Polyhalogenated 2,5-Diphenylbicycloocta-1,5,7-trienes
Roedig, Alfred,Ganns, Eva Maria
, p. 406 - 419 (2007/10/02)
Nucleophilic reagents attack 1b-d on the four-membered ring with aromatization of the six-membered ring by elimination of chlorine.With methoxide di- and tetrasubstituted products 4a,b and 5b are formed, with thiolates however compounds 8, 9, 10, and 11 with 1, 2, and 4 substituents can be obtained.The reaction of 1b-d with primary amines leads to the diimines 12 or monoimines 13, while secondary amines cause ring opening to 16 or formation of the aminophthalides 20. - Cyclooctatetraene rearrangement of 1b and c in formic acid or in the presence of Ag+ -ions is complicated by the competing thermal rearrangement 1b,c -> 2b,c and numerous by-products. 3b and c were isolated only in 15 and 10percent yield, respectively.The mechanism of the nucleophilic substitutions is discussed.
