Oxidations with IBX: benzyl halides to carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones

نویسندگان

  • Jarugu Narasimha Moorthy
  • Nidhi Singhal
  • Kalyan Senapati
چکیده

A variety of benzyl halides were converted to the corresponding aldehydes/ketones in respectable yields by IBX in DMSO at 65 C. The bromohydrin reaction of olefins using NBS–H2O in DMSO can be nicely adapted to IBX-mediated oxidation of benzyl halides in such a way that olefins are converted to the corresponding 1,2-diketones in good isolated yields in one-pot. 2006 Elsevier Ltd. All rights reserved. The oxidation of halides to the corresponding carbonyl compounds constitutes an important transformation in synthetic organic chemistry (Eq. 1). The oldest method for such a conversion constitutes the Hass–Bender reaction, which involves O-alkylation of the nitronate anion followed by decomposition of the resulting intermediate. The Sommelet reaction is another well-known reaction to effect this transformation, and involves the use of hexamethylenetetramine to afford the formaldehyde 0040-4039/$ doi:10.1016/ * Correspon 2597436; e Br

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تاریخ انتشار 2006