137676-34-7Relevant articles and documents
Partially Fluorinated Heterocyclic Copmpounds. Part 27. The Synthesis of 4,5,6,7-Tetrafluorobenzothiophene and 4,5,6,7,8,9-Hexafluoronaphthothiophene; some Chemistry and Electrochemistry
Brooke, Gerald M.,Mawson, Simon D.
, p. 1919 - 1923 (2007/10/02)
2,3,4,5,6-Pentafluorobenzyl methyl sulphoxide (6) is readily converted by butyl-lithium into 4,5,6,7-tetrafluorobenzothiophene (8) and 1,3,4,5,6,7,8-heptafluoro-2-naphthylmethyl methyl sulphoxide (9) in a similar manner gives a very low yield of 4,5,6,7,8,9-hexafluoronaphthothiophene (11) accompanied by the 7- and 8-butylated derivatives (12) and (13) respectively, and also 1,3,4,5,6,7,8-heptafluoronaphthalene-2-carbaldehyde (10).Compound (8) undergoes Diels-Alder addition reactions followed by sulphur elimination with dimethyl acetylenedicarboxylate and tetrafluorbenzyne to give the naphthalene and anthracene derivatives (14) and (15) respectively.With lithium propane-2-thiolate, compound (8) gives the 5-propan-2-ylthio and 5,6-bispropan-2-ylthio derivatives (16) and (17) respectively.Compound (8) is polymerised by SbF5-HF to poly(1,3-dihydro-4,5,6,7-tetrafluorobenzo-thiophene) (20).The electrochemical anodic oxidation of (8) has been studied extensively: polymer (20) is produced accompanied by a deep red material readily soluble in chloroform, which is not poly(4,5,6,7-tetrafluorobenzothiophene) (24).
