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Nucleophilic Addition to $\alpha$, $\alpha$-Dihalogenocarbonyl Compounds: Synthetic and Mechanistic Implications

Chandrasekhar, Sosale and Murthy, Tara (1987) Nucleophilic Addition to $\alpha$, $\alpha$-Dihalogenocarbonyl Compounds: Synthetic and Mechanistic Implications. In: Journal of Chemical Research, Synopses (12). pp. 414-415.

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Hydride reduction of dibromoketones $RCOCHBr_2$ $(R=Ph, CMe_3)$ gave $RCH(OH)CHBr_2$, which, when treated with KOH in $CCl_4$, gave aldehydes RCHBrCHO via intermediate bromoepoxides I. Grignard dialkylation of $Cl_2CHCOCl$ gave chloroalcs. $Cl_2CHCR_{12}OH$ $(II, R_1=Me, Ph, PhCH_2)$ in 85-96% yields. Similar rearrangement of II with KOH in $CCl_4$ gave the corresponding chloroaldehydes $R_{12}CClCHO$.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Ramya Krishna
Date Deposited: 28 Apr 2008
Last Modified: 27 Aug 2008 13:20
URI: http://eprints.iisc.ac.in/id/eprint/13790

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