PubMed · 763339
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C Lloyd. 1979-02-15. Poles apart?. https://doi.org/10.1038/277515b0
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Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.
[Structure: see text] In addition reactions of enecarbamates and enamides, extremely high turnover frequency of the catalyst was observed in comparison with that of silicon enolate addition reactions. This is presumably due to fast transfer of the proton that locates on the nucleophiles.
Facile, selective and sensitive spectrophotometric method has been developed for the determination of carbosulfan in insecticidal formulations, fortified water, food grains, agriculture wastewater and soil samples with newly synthesized reagents. The method was based on acid and alkaline hydrolysis of the carbosulfan pesticide, and the resultant hydrolysis product of carbosulfan was coupled with 2,6-dibromo-4-methylaniline to give a yellow color product with lambda(max) of 464 nm or interaction with 2,6-dibromo-4-nitroaniline to produce yellow colored product with lambda(max) of 408 nm or coupling with 2,4,6-tribromoaniline to form red colored product has a lambda(max) of 471 nm. Under optimal conditions, Beer's law range for 2,6-dibromo-4-methylaniline (DBMA) was found to be 0.2-12.0 microg ml(-1), 0.6-16.0 microg ml(-1) for 2,6-dibromo-4-nitroaniline (DBNA) and 0.4-15.0 microg ml(-1) for 2,4,6-tribromoaniline (TBA). The molar absorptivity of the color systems were found to be 3.112 x 10(4) l mol(-1) cm(-1) for DBMA, 3.214 x 10(4) l mol(-1) cm(-1) for DBNA and 3.881 x 10(4) l mol(-1) cm(-1) for TBA. Sandell's of the color reactions are 0.013 microg cm(-2) (DBMA), 0.012 microg cm(-2) (DBNA) and 0.011 microg cm(-2) (TBA) respectively. The effect of the non-target species on the determination of carbosulfan was studied to enhance the selectivity of the proposed methods. The formation of colored derivatives with the coupling agents is instantaneous and stable for 28, 30, and 26 h. Performance of the proposed methods were compared statistically in terms Student's F and t-tests with the reported methods.