Chemistry of α-nitroepoxides: synthesis of useful intermediates via nucleophilic ring opening of α-nitroepoxides

Vankar, Yashwant D. ; Shah, Kavita ; Bawa, Anita ; Singh, Surendra P. (1991) Chemistry of α-nitroepoxides: synthesis of useful intermediates via nucleophilic ring opening of α-nitroepoxides Tetrahedron, 47 (42). pp. 8883-8906. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)81002-4

Abstract

Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3·Et2O(or ClSiMe3). In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitro-cyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis. Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.

Item Type:Article
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ID Code:58303
Deposited On:31 Aug 2011 06:34
Last Modified:31 Aug 2011 06:34

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