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The instability of hydroxyl peroxyesters, the elusive Criegee intermediates of the Bayer-Villiger rearrangement, can be alleviated by selective deactivation of stereoelectronic effects that promote the 1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within a five-membered ring can be prepared by mild reduction of respective hydroperoxyl peroxyesters (β-hydroperoxy-β-peroxylactones) which were formed in high yields in reaction of β-ketoesters with BF3·Et2O/H2O2.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
In the theoretical calculations reported here, we show that the hydration of the Criegee intermediate within the sub-nanospace of fullerene cages occurs differently in different fullerenes, thereby pr...
We have discovered synthetic access to β-hydroperoxy-β-peroxylactones via BF-catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, ...
Manipulating the regioselectivity of Baeyer-Villiger （BV） reactions remains an ongoing issue in organic chemistry, be it by synthetic catalysts or enzymes of the type Baeyer-Villiger monooxygenase...
Recent, direct studies have shown that several reactions of stabilized Criegee intermediates (SCI) are significantly faster than indicated by earlier indirect measurements. The reaction of SCI with SO...
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Ordered rearrangement of T-cell variable gene regions coding for the antigen receptors.
The ordered rearrangement of gene regions by DNA recombination such as that which occurs normally during development.
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Ordered rearrangement of B-lymphocyte variable gene regions coding for the IMMUNOGLOBULIN CHAINS, thereby contributing to antibody diversity. It occurs during the differentiation of the IMMATURE B-LYMPHOCYTES.
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