SCOPUS 정보 검색 플랫폼

Volumn , Issue 1, 2008, Pages 0055-0060

1,2-Diarylethenyl sulfones: Readily-prepared masked diarylethynes for access to aryleneethynylenes

Author keywords

Aldehydes; Alkynes; Arylene ethynylenes; Eliminations; Sulfones

Indexed keywords

ACETYLENE; BENZALDEHYDE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; SONOGASHIRA REACTION;

EID: 38549116540 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990924 Document Type: Article

Times cited : (12)

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28
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- Typical Procedures 1-(3-Bromophenyl)-2-(3-iodophenyl)-1, phenyisulfonyl)ethene (4a, To a THF solution (30 mL) of 3-bromophenylmethyl phenyl sulfone (2.00 g, 6.4 mmol) was added a THF solution of LiHMDS (1.0 M, 7.0 mL, 7.0 mmol) at -78°C, and the mixture was stirred for 0.5 h. A THF solution (8 mL) of 3-iodobenzaldehyde (1.24 g, 5.3 mmol) was added at -78°C, and the mixture was stirred for 1 h. Diethyl chlorophosphate (0.75 mL, 5.4 mmol) was added at -78°C, and the mixture was stirred at r.t. for 1 h. A THF solution of LiHMDS (1.0 M, 5.4 mL, 5.4 mmol) was added at -78°C, and the mixture was stirred at r.t. overnight. After usual workup with EtOAc-aq NH4Cl, the organic layer was evaporated, and the residue was subjected to column chromatography on silica gel (10% EtOAc-hexane) to furnish 4a (2.24 g, 80, Compound 4a: E/Z, 88:12 the geometry of E- or Z-isomers was not determined, several signals overlapped in 13
- 3): δ = 55.2, 87.1, 88.2, 89.9, 90.2, 114.0, 115.0, 122.1, 123.0, 124.0, 125.0, 128.4, 129.7, 130.1, 130.9, 131.4, 131.5, 133.1, 134.3, 134.4, 159.7.

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