Bromohydrin formation in dimethyl sulfoxide
About: This article is published in Journal of the American Chemical Society.The article was published on 1968-09-01. It has received 158 citations till now. The article focuses on the topics: Dimethyl sulfoxide.
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TL;DR: The use of bromine and different bromo-organic compounds in organic synthesis is outlined and the scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc is described briefly.
Abstract: Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.
343 citations
TL;DR: The highly strained ingenane skeleton was constructed through an intramolecular cyclization reaction of an acetylene dicobalt complex followed by a rearrangement Reaction of an epoxy alcohol.
Abstract: Total synthesis of ingenol, a diterpene isolated from the genus Euphorbia, was accomplished on the basis of the novel key reactions. The highly strained ingenane skeleton was constructed through an intramolecular cyclization reaction of an acetylene dicobalt complex followed by a rearrangement reaction of an epoxy alcohol. The C(3),C(4),C(5)-triol moiety was introduced by a stereoselective double dihydroxylation reaction of a diene having C(2)−C(3) and C(4)−C(5) double bonds.
142 citations
126 citations
TL;DR: The experimental basis for the proposed modes of activation for iodine catalysis is summarized and typical iodine-catalyzed reactions are analyzed to gain more insights into the underlying reaction mechanisms.
Abstract: Molecular iodine has been used for more than 100 years as a remarkable catalyst for many organic transformations such as cycloadditions, Michael and aldol reactions, or esterifications. Different explanations for the origin of its catalytic effect have been proposed in the last decades including a "hidden" Bronsted acid catalysis by HI, a Lewis-acid (or halogen-bond) activation, or catalysis by an iodonium(I) species. Recently, iodine catalysis again gained more interest due to the latest developments in halogen-bond catalysis. In this Minireview, we first summarize the experimental basis for the proposed modes of activation. Subsequently, we analyze typical iodine-catalyzed reactions to gain more insights into the underlying reaction mechanisms.
114 citations
TL;DR: The key step of the synthesis involves the reaction of glycals [3,4,6,tri-O-acetyl-D-glucal (1), the new glycal derivative 4-Oacetyl, 1,5-anhydro-2,6-dideoxy-3,C-methyl,3,O-methyl-L-ribo-hex-1-enitol (2,2), and 3-acetamido-4, 6-di-O -acetyl -1, 5-anhedro-
111 citations