Premium
Band‐Shaped Structures by Repetitive Cycloaddition Reactions of Benzo[1,2‐ b :4,5‐ b ′]bisthiete
Author(s) -
Meier Herbert,
Rose Bernd,
Schollmeyer Dieter
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970619
Subject(s) - chemistry , cycloaddition , yield (engineering) , bent molecular geometry , dehydration , thermal decomposition , scheme (mathematics) , stereochemistry , medicinal chemistry , organic chemistry , thermodynamics , biochemistry , catalysis , mathematical analysis , physics , mathematics
Benzo[1,2‐ b :4,5‐ b ′]bisthiete ( 1 ) undergoes stepwise thermal opening of the 4‐membered rings, thereby generating two highly reactive 8π systems (Scheme 1). In the presence of 1,4‐dihydro‐1,4‐epoxynaphthalenes 2 , the dithiaheptacene derivatives 3 are formed, dehydration of which leads to the compounds 4 and 5 (Scheme 2). Repetitive cycloaddition reactions of 1 with the twofold 2π component 11 (Scheme 3) yield the oligomers 15 with statistically bent (and possibly cyclic) structures (Schemes 4 and 5). While 15 and the related oligomers 14 are freely soluble in many organic solvents, the dehydrated systems 16 (Scheme 6) are totally insoluble.