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Band-Shaped Structures by Repetitive Cycloaddition Reactions of Benzo[1,2-b:4,5-b′]bisthiete (1997)

Meier, Herbert ; Rose, Bernd ; Schollmeyer, Dieter

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1173-1177

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ISSN: 0947-3440

Keywords: Dithiaheptacenes ; Molecular ribbons, bent, cyclic ; [8 + 2] Cycloaddition reactions ; Arenes ; Polycycles ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970619

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