MOLECULAR AND CRYSTALLINE STRUCTURE OF FURFURAL DIACETATE NITRATION INTERMEDIATE

Article abstract of DOI:10.1016/0040-4020(80)80080-9

X-ray crystallography established the structure of the acetyl nitrate adduct to furfural diacetate (H.Gilman and G.F.Wright (1930)) as trans-2-acetoxy-5-nitro-2,5-dihydro-2-furfural diacetate (1a).The furanoid ring is essentially planar, its geometry being similar to that of 2,5-dihydrofuran molecule, except for the interatomic distance C(3)-C(4) which is shorter than the corresponding length of double C-C bond in alkenes.The C(5)-N 1.52 Angstroem bond significantly exceeds the standard C-N bond lengths in nitroalkanes and nitrobenzene.