Catalytic application of sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (SA-MNPs) for protection of aromatic carbonyl compounds and alcohols: experimental and theoretical studies

摘要

Protection techniques of functional groups within the structure of organic compounds are important synthetic methods against unwanted attacks from various reagents during synthetic sequences. Acetal and thioacetal groups are well known as protective functional groups in organic reactions. In this study, acetalization of carbonyl compounds with diols and dithiols and methoxymethylation of alcohols with formaldehyde dimethyl acetal (FDMA) have been carried out using sulfamic acid-functionalized magnetic Fe _(3) O _(4) nanoparticles (SA-MNPs) as a heterogeneous solid acid catalyst. Products were characterized by FT-IR and NMR spectroscopies. The structural and electronic properties of some products were computed by quantum mechanical (QM) methods. Depending on the stereochemistry and electronic properties that were obtained by computational results, we have suggested that hyperconjugation plays a key role in the structural properties of 2-phenyl-1,3-dioxolane derivatives, and also the electron transfer between π-electrons of the aromatic ring with the 3d orbital of S-atoms influences the 2-phenyl-1,3-dithiane derivatives' structure.