An improved procedure for the isolation of the main addition products of the reaction between nitronium acetate and furfural diacetate or methyl 2-furoate is described.The kinetics of the deacetylation of the diastereomeric 1,4-adducts in buffer solutions revealed a substantial primary hydrogen isotope effect.Mild acid-induced alcoholysis transformed the adducts into 2,5-dialkoxy-2,5-dihydrofurans.The reaction chemistry of the furan adducts is compared with the solvolytic pathways reported for ipso nitronium acetate adducts formed from alkylbenzenes.
MOLECULAR AND CRYSTALLINE STRUCTURE OF FURFURAL DIACETATE NITRATION INTERMEDIATE
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.
Mishnev, A. F.,Bleidelis, J. J.,Venters, K. K.
p. 1817 - 1820
(2007/10/02)
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