Abstract
AbstractMonoaldehydes and dialdehydes are parts of millions of compounds and are extremely versatile intermediates. For the synthesis of monoaldehydes, one impressive approach to date, because of its excellent selectivity, high yield and stability towards over-oxidation and over-reduction, is the oxidation of organic monohalides. Numerous monohalides oxidation based methodologies to afford monoaldehydes are disclosed in literature. In this research work, twelve well-known approaches (well-documented for synthesis of monoaldehydes from monohalides) are investigated for their effectiveness towards synthesis of organic dialdehydes from organic dihalides. The classical approaches under investigation include modified Sommelet oxidation, Kröhnke oxidation, sodium periodate-mediated oxidative protocol, manganese dioxide-based oxidative approach, Kornblum oxidation and Hass-Bender oxidation. The eco-friendly approaches under observation include periodic acid-based IL protocol, periodic acid in vanadium pentoxide-mediated IL method, hydrogen peroxide in vanadium pentoxide-based approach, hydrogen peroxide-mediated IL methodology, IBX-assisted IL protocol and bismuth nitrate-promoted IL technique. In this investigation yield, overoxidation, eco-friendliness, cost-effectiveness and recyclability are the main parameters which are under examination. Hopefully, this research will help chemists in carrying out routine operations in organic synthesis and will also be fruitful to select finest synthetic approach, develop further new transformational methodologies and improve current transformational approaches for the synthesis of dialdehydes.
Highlights
In this research work, twelve well-known approaches known and important entities
The high suitability of this transformational approach is due to three reasons: (i) usually it prevents over-oxidation and over-reduction which are very frequent in indirect methods, for example, in the process of conversion of organic dialcohols to dialdehydes overoxidation is a common phenomenon whereas in the production of dialdehydes from the transformation of organic diacids or diesters over-reduction occurs very frequently, (ii) generally organic dihalides-mediated conversion offers high selectivity and (iii) in the majority of cases outstanding yield is attained [10,11]
In literature, most organic halide-based transformational techniques are concerned with the synthesis of monoaldehyde and good research has been less targeted in the field of synthesis of dialdehydes from organic dihalides [12]
Summary
Except 1, 12 and 19, all reagents and other chemicals were obtained from Fluka, Merck and Sigma-Aldrich. The precursor 1 was prepared by the two-step reported method of Mancilha et al [13] and Page et al [14], precursor 12 was prepared according to the reported method of Asakawa et al [15] and precursor 19 was obtained through the procedure of Pesin et al [16]. All reagents and other chemicals were used without additional purification, while all the solvents were purified through distillation before use. Proton and carbon nuclear magnetic resonance spectra were measured at 300 MHz on a Varian Gem2300 300 MHz spectrometer. Tetramethylsilane (TMS) as an internal standard and dimethyl sulfoxide (DMSO) as solvent were used. Chemical shifts were expressed in ppm units. The structural characterizations are given except for those compounds which are commercially available
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