CHEMISTRY OF NITRO COMPOUNDS .5. CHEMISTRY OF ALPHA-NITROEPOXIDES - SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING-OPENING OF ALPHA-NITROEPOXIDES

Various alpha-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 alpha-nitrocyclopentene oxide 6 and alpha-nitrocyclohexene oxide 7 to form the corresponding alpha-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.