Radical initiation using borole derivatives

Tetrahedron Letters

Volumn 49, Issue 4, 2008, Pages 628-630

  Montgomery, Isabella ^a   Parsons, Andrew F ^a   Ghelfi, Franco ^b   Roncaglia, Fabrizio ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPYLBENZO[D][1,3,2]DIOXABOROLE DERIVATIVE; BORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROBORATION; SYNTHESIS;

EID: 37549070722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.142     Document Type: Article

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39. 3 (0.76 ml, 2.82 mmol, 1.1 equiv) and bromoacetophenone (1) (0.50 g, 2.50 mmol, 1 equiv) were added and the reaction stirred overnight in air. Purification by column chromatography (KF on silica; petrol-EtOAc, 1:1) gave acetophenone (0.39 g, 99%) as a colourless oil. (Catechol byproducts may be removed from the organic product, prior to chromatography, by washing a solution of the crude product in EtOAc with 1 M NaOH).
40. 1H NMR spectrum indicated mainly unreacted PBD.
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42. 3SnH (1.1 equiv).
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45. -1.
46. PBD (8) can be used to polymerise other alkene monomers, at rt, including butyl acrylate, methyl acrylate, methacrylic acid and acrylamide. Parsons, A. F.; Sharpe, D. J.; Taylor, P. unpublished results.