Tetrahedron

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

YD Vankar, K Shah, A Bawa, SP Singh

Index: Vankar, Yashwant D.; Shah, Kavita; Bawa, Anita; Singh, Surendra P. Tetrahedron, 1991 , vol. 47, # 42 p. 8883 - 8906

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Citation Number: 31

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 ...

~75%

~81%

~40%

~61%

~92%

~86%

~78%

~78%

~72%

~75%

~62%

~65%

~82%

~70%

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