79977-66-5Relevant academic research and scientific papers
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.
Polyhalogenated Bicycloocta-1,5,7-trienes, VIII Synthesis and Cyclodimerization of Polyhalogenated 2-Phenyl- and 2-Pentachlorophenyl Substituted Butenynes
Roedig, Alfred,Ganns, Eva Maria,Henrich, Christian,Schnutenhaus, Horst
, p. 1674 - 1684 (2007/10/02)
Starting material for the synthesis of the butenynes 1c-e is the aldehyde 4 which can be converted into 1c via 9 or 5 and 10 as well as into 1d via 8.In the four-step synthesis of 1e the decisive reaction is the perchlorination of the phenyl group in 6 to
