Hypervalent Iodine Chemistry by Thomas Wirth (eds.) PDF

By Thomas Wirth (eds.)

ISBN-10: 3319337319

ISBN-13: 9783319337319

ISBN-10: 3319337335

ISBN-13: 9783319337333

The sequence issues in present Chemistry offers serious stories of the current and destiny traits in smooth chemical learn. The scope of insurance is all parts of chemical technological know-how together with the interfaces with similar disciplines akin to biology, drugs and fabrics technology. The objective of every thematic quantity is to offer the non-specialist reader, no matter if in academia or undefined, a complete perception into a space the place new examine is rising that's of curiosity to a bigger medical viewers. each one evaluation in the quantity significantly surveys one point of that subject and locations it in the context of the quantity as a complete. the main major advancements of the final five to ten years are provided utilizing chosen examples to demonstrate the rules mentioned. The assurance isn't really meant to be an exhaustive precis of the sector or comprise huge amounts of information, yet should still otherwise be conceptual, targeting the methodological pondering that would let the non-specialist reader to appreciate the data provided. Contributions additionally supply an outlook on strength destiny advancements within the box. evaluate articles for the person volumes are invited through the amount editors. Readership: examine chemists at universities or in undefined, graduate students.

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Extra resources for Hypervalent Iodine Chemistry

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1). Generally speaking, phenols are mildly acidic electronrich aromatic nucleophiles. They are highly sensitive to one-electron oxidation into delocalized phenoxy radical species, and can also be converted into cationic electrophiles of the phenoxenium type or equivalents thereof by two-electron oxidation or activation through the use of “phenolophile” (oxidizing) metal- or halogen-based reagents. Their non-aromatic cyclohexadienone tautomers can also be stabilized through the formation of transition metal–arene complexes, which can then render them prone to cycloaddition and nucleophilic addition processes.

Later on, Harned’s group explored another desymmetrization method based on a Pd-catalyzed acetoxylation-cyclization of 450 -type alkyne-tethered cyclohexa-2,5dienones 75, which were generated by a DIB- or BTI-mediated dearomatization of para-substituted phenols 51 in the presence of propargyl alcohol or but-2-yn-1-ol as solvent (Fig. 20). The control of stereoselectivity of the Pd-catalyzed cyclization event was brought by the use of the pinene-derived bipyridine ligand 76, but enantiomeric excesses of only up to 62% could be obtained for the formation of the bicycles 77 [68].

The λ5-iodanes 2-iodylbenzenesulfonic acids (IBS) [35, 36] that are thus generated in situ by the action of Oxone®, such as the 5-Me-IBS, regioselectively convert naphthols [including 2-methoxy-1-naphthol (1i)] [37], phenanthrols, or simple phenols into ortho-quinones, as exemplified in Fig. 5, except in the case of 3-methoxy-1naphthol (1k), for which the oxidation was para-selective as a likely consequence of a directing effect of the electron-donating meta-methoxy group [34]. The rich topic of the utilization of ortho- and para-quinones in chemical synthesis falls outside the scope of this review, but there is a quite elegant and 30 S.

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Hypervalent Iodine Chemistry by Thomas Wirth (eds.)


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