Refernces
10.1016/j.jorganchem.2003.10.040
The study presents the synthesis and comprehensive characterization of 4-Me2NC6H4HgOH, the first verified organomercury hydroxide that crystallizes as discrete molecules in the solid state. The researchers detail its preparation from 4-Me2NC6H4HgOAc and discuss the structures of related compounds, including 4-Me2NC6H4HgOAc and (4-Me2NC6H4)2Hg. The study delves into the complex history of organomercury hydroxides, resolving previous conflicting reports and misconceptions about their existence and properties. It also explores the behavior of these compounds in aqueous solution, pointing to pH-dependent equilibria involving various species. The researchers used techniques such as electrospray mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, and X-ray crystallography to characterize the compounds. The results provide a clear structural and spectral signature of 4-Me2NC6H4HgOH, confirming its status as a true organomercury hydroxide and contributing to a better understanding of arylmercury chemistry.
10.1007/BF00904131
The study focuses on an improved synthesis of d,l-serine from acrylsulfonic acid ethyl ester. The researchers aimed to develop a more efficient and cost-effective method for synthesizing d,l-serine, building on the work of du Vigneaud and Wood. The process involves several key steps: Initially, a,?-dibromopropionic acid ethyl ester (I) is synthesized by reacting acrylsulfonic acid ethyl ester with bromine. This compound (I) is then converted to a-bromo-?-ethoxypropionic acid ethyl ester (II) using sodium ethylate in the presence of catalytic amounts of mercury(II) acetate in absolute alcohol. The presence of mercury(II) salts and the water content of the medium are identified as crucial factors in directing the reaction towards the desired product. The bromine in compound (II) is subsequently replaced by an azide group to form a-azido-?-ethoxypropionic acid ethyl ester (III), which is then reduced to a-amino-?-ethoxypropionic acid ethyl ester hydrochloride (IV) using catalytic hydrogenation. Finally, the ethyl ester (IV) is hydrolyzed to yield d,l-serine hydrobromide (V), which is purified to obtain d,l-serine (VI). The study highlights the importance of reaction conditions and catalysts in achieving high yields and purity of the final product, with an overall yield of 61% for the synthesis of d,l-serine from the starting material.
10.1246/cl.1982.1715
The research aimed at synthesizing compounds related to sclerosporal, a metabolite of Sclerotinia flucticola, to confirm its proposed guaianoid structure. The researchers synthesized two optically active aldehydes, 3 and 4, which were thought to possess the planar structure for sclerosporal. Starting from (-)-carvone, various chemicals were used in the process, including 1,3-dibromo-2-pentene for alkylation, Hg(OAc)2 and HCO2H for treatment to yield diones and formates, DDQ for dehydrogenation, and Li-NH3 for reduction. The study concluded that the proposed structures for sclerosporal and sclerosporin were erroneous, as the synthetic aldehydes 3 and 4 did not match the spectral data of natural sclerosporal, necessitating a revision of the structures. The research also highlighted the importance of further studies to confirm the suggested mechanisms of the reactions involved.
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