Ferrocenyl-substituted fluorescent anthracenes and anthraquinones

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 467-472

  Butler, Ian R ^a   Callabero, Alfonso G ^a   Kelly, Glenn A ^a   Amey, Jennifer R ^a   Kraemer, Tobias ^a   Thomas, Dafydd A ^a   Light, Mark E ^b   Gelbrich, Thomas ^b   Coles, Simon J ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Anthracene; Anthraquinone; Ferrocene

Indexed keywords

1,1 BIS(2 ETHENYLANTHRAQUINOYL)FERROCENE; ANTHRACENE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; FERROCENE DERIVATIVE; FLUORESCENT DYE; LITHIUM DERIVATIVE; PHENYLETHYNYLLITHIUM; TIN CHLORIDE; TRIMETHYLSILYLETHYNYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; CIS TRANS ISOMERISM; CRYSTAL STRUCTURE; CRYSTALLIZATION; REDUCTION; SUBSTITUTION REACTION; SUZUKI REACTION; X RAY DIFFRACTION;

EID: 0346363698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.013     Document Type: Article

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48. A typical synthetic procedure is as follows: A solution of either phenyllithium or 2-thienyllithium (1 mol equiv) in dry diethyl ether (100 mL) was cooled to ca. -70°C and 0.4 mol equiv of the 1-ferrocenylanthraquinone was added. After warming to room temperature the mixture was hydrolysed by addition of water (ca. 50 mL). The organic layer was then separated and the water layer was re-extracted with several portions of ether until the extracts were pale coloured. The combined organic layers were then reduced in volume to a give a deep red oil. The resultant oil was suspended in a mixture of acetic acid/water (50/50, 50 mL) and diethyl ether (50 mL) and a large excess of tin chloride dihydrate (5 mol equiv) was added. The mixture was stirred for 10 h. The organic layer was separated and further diethyl ether was added. The solution was then carefully washed with a dilute sodium carbonate solution before being reduced in volume and chromatographed on silica. The products (50-65%) were isolated as bright orange solids eluting with a mixture of petrol and diethyl ether (1:1).
49. Typical procedure for the deprotection of silylacetylenes: example: 9,10-bis(trimethylsilylethynyl)anthracene (0.5 g, 1.35 mmol) was dissolved in tetrahydrofuran (50 mL) in a Schlenk tube under nitrogen. Tetra-n-butylammonium fluoride (0.71 g, 2.70 mmol) was added to the solution. An immediate colour change from orange to brown occurred. The solution was left to stir for 1 h. The solution was then purified by column chromatography on silica using petrol as the eluent. The analogous ferrocenyl compounds can be treated similarly although the method has yet to be optimised because of the product sensitivity.
50. 2 Fe. The product was also characterised by crystallography, details of which will be published separately. Yield 88%.
51. H4,H3=7.90 Hz, anthraquinonyl H-4), 7.87-7.89 (m, 2H, anthraquinonyl-H), 7.98-8.00 (m, 2H, anthraquinonyl-H).