The synthesis of the novel 1‐(substituted phenoxy/phenyl)‐2‐phospholene and phospholane 1‐oxide derivatives, which are analogs of sugars having a phosphorus atom in place of the ring oxygen of normal sugars, is described. All of the synthesized derivatives are structurally characterized by multi nuclear NMR, mass, and IR spectral data, elemental and X‐ray crystallographic analyses.

A convenient and facile chemo-and regioselective oxidation of the allylic methylene group in a 2-phospholene ring system afforded the novel carbonyl derivatives of 2-phospholenes (2a-i). The method gives high conversion and selectivity in the formation of allylic ketones. The advantages of this ox-idation method in such a five-membered pseudo sugar 2-phospholene ring are mentioned, and the oxidation is examined on several substituted 2-phospholenes (1a-i).

3 in the presence of NaH by using benzyl bromide or methyl iodide as electrophiles afforded the target title compounds.

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Allylic oxidation of 2-phospholenes gave the first successful preparation of 4-oxo-2-phospholene 1-oxide derivatives, and this synthetic approach provides a ready accessible route in the synthesis of a wide variety of pentofuranose analogs of phospha sugars, having a phosphorus atom as the sugar ring hetero atom.