147462-17-7

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 147462-20-2 (3,4-Dimethyl-2,5-dihydro-furan-2-yl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Development of new transition metal catalysts for the oxidation of a hydroxamic acid with in situ Diels-Alder trapping of the acyl nitroso derivative

New transition metal catalysts have been prepared and applied for in situ formation of acyl nitroso dienophiles. The Royal Society of Chemistry.

Mechanistic insights into transition metal-catalysed oxidation of a hydroxamic acid with in situ Diels-Alder trapping of the acyl nitroso derivative

New insights into the mechanism for the transition metal-mediated oxidation of hydroxamic acids to give intermediate acyl nitroso species, with subsequent hetero-Diels-Alder trapping are presented. The activation of triphenylphosphine-ligated ruthenium-salen complexes is examined, and evidence is presented for the ruthenium-oxo species which are involved in the oxidative process of the hydroxamic acid. The observation of the lack of asymmetric induction involved in the intermolecular cycloaddition process involving the intermediate acyl nitrsoso species is explained, with the aid of comparing the ruthenium-salen-based systems with nitrosotoluene, and copper(I)/copper(II) BINAP-based catalysis of nitrosopyridine complexes. This study demonstrates the importance of secondary coordination to achieve asymmetric induction in nitroso-Diels-Alder reactions.

Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions

The acyl nitroso Diels–Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3-dienes and hydroxamic acids, giving up to 96 % isolated yield.

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. Th

Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: Efficient and practical access to nitroso compounds

A general and efficient aerobic oxidation of N-substituted hydroxylamines is described. The mild reaction conditions employed provide a catalytic and sustainable alternative to stoichiometric oxidation methods to gain access to a range of nitroso compound

Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic acids and hydrazides to acyl-nitroso and Azo intermediates, and their Diels-Alder trapping

CuCl2, in the presence of a 2-ethyl-2-oxazoline ligand, is an effective catalyst for the room temperature, aerobic oxidation of hydroxamic acids and hydrazides, to acyl-nitroso and azo dienophiles respectively, which are efficiently trapped in