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Synlett

Volumn , Issue 16, 2007, Pages 2559-2563

Synthesis and photoluminescence studies of siloles with arylene ethynylene strands

(5) Ding, Changhua a Babu, Govindarajulu a Orita, Akihiro a Hirate, Takayoshi a Otera, Junzo a

a OKAYAMA UNIVERSITY OF SCIENCE (Japan)

Author keywords

Aldehydes; Alkynes; Eliminations; Siloles; Sulfones

Indexed keywords

ALKENE DERIVATIVE; HETEROCYCLIC COMPOUND; PHENYLENE ETHYNYLENE DERIVATIVE; SILOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ELIMINATION REACTION; FLAME PHOTOMETRY; PHOTOCHEMISTRY; PHOTOLUMINESCENCE; SONOGASHIRA REACTION; SYNTHESIS;

EID: 35348949630 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-986641 Document Type: Article

Times cited : (22)

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- Representative Experimental Procedure: (i) Preparation of 3e: To a THF solution (40 mL) of phenyl 4-(trimethylsilylethynyl)phenylmethyl sulfone (1.57 g, 4.8 mmol) was added LiHMDS (4.8 mL, 1.0 M THF solution, 4.8 mmol) at -78°C, and the mixture was stirred for 0.5 h. To this solution was added a THF solution (5 mL) of 2,5-diethyl-4-(4-methoxyphenylethynyl)benzaldehyde (1.16 g, 4.0 mmol, and the mixture was stirred for 1 h. After CIP(O)(OEt)2 (0.694 mL, 4.8 mmol) had been added, the mixture was stirred at r.t. for 2 h. After LiHMDS (20.0 mL, 1.0 M THF solution, 20.0 mmol) had been added at -78°C, the reaction mixture was stirred at -78°C for 1 h and then at 30°C for 17 h. After usual workup with EtOAc and aq NH4Cl, the organic layer was dried over MgSO4 and filtered. The solvents were evaporated, and the residue was chromatographed (CH2Cl 2-hexane, 3:7) to give 3e 1.73 g, 94, as a colorless solid
- 2Si: 1063.49; found: 1063.1.

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