Abstract
The N-trimethylsilyl compounds of the cyclic imides derived from cis-cyclohexan-1,2-dicarboxylic acid, cis-4-cyclohexen-1,2-dicarboxylic acid and phthalic acid were prepared. Reaction of the N-silylated cyclic imides 2 and 10 with 1,2,3,5-tetra-O-acetyl-β-ᴅ-ribofuranose in the presence of tin tetrachloride yielded the appropriate unusual ribonucleosides 4 and 12 whereas 14 led only to traces of the ribosylated derivative. The silylation and ribosylation sites in the aforementioned bicyclic imides were proved by 1H, 13C, and 29Si NMR spectroscopy and compared with data found for the monocyclic imides N-succinimide and N-maleinimide.
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