Oxidation of dihydrazones of diaryl α-diketones to diarylacetylenes using sodium periodate

Chemistry Letters

Volumn 39, Issue 12, 2010, Pages 1279-1280

  Takale, Balaram S ^a   Telvekar, Vikas N ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78649811234     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.1279     Document Type: Article

References (35)

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29. Experimental procedures: Representative procedure for preparation of diarylacetylene. Synthesis of 1b (Table 1): NaIO4 (898 mg, 4mmol) in biphasic system water:EtOAc (10 mL) was stirred at room temperature for 5min, then 1a (500 mg, 2mmol) was added to the stirred solution. Finally the reaction mixture was stirred for 1 h and completion of reaction was confirmed by thin layer chromatography (5%, hexane:EtOAc). Reaction mixture was then diluted with water and extracted with CHCl3 (3 × 10 mL), dried with Na2SO4, filtered, and concentrated in vacuo to isolate crude residue, which was further subjected to silica gel column chromatography using mixture of hexane:EtOAc (10:1) to get final pure product 1b. Representative procedure for deprotection of monohydrazone. Synthesis of 14b (Table 2): NaIO4 (954 mg, 2.2mmol) in water:EtOAc (10 mL) was stirred at room temperature for 5min, then 14a (500 mg, 2.2mmol) was added to the stirred solution. Finally reaction mixture was stirred for 30min, and after completion of reaction the product 14b was isolated as described for 1b. Detailed experimental procedure and spectral data of all compounds are given in Supporting Information which is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
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