Seleno- and Telluroaldehydes and -ketones

Guziec, Lynn J.; Guziec, Frank S.

doi:10.1016/b0-08-044655-8/00054-4

Cited by 6 publications

(2 citation statements)

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“…Replacement of an oxygen atom in ordinary organic compounds with heavier elements, such as sulfur or selenium, allows for unique reactivities and properties in the resulting compounds. Selenium isologues of carbonyl compounds, i.e., selenocarbonyl compounds, such as selenoaldehydes and -ketones, , have absorption spectra in the visible region, and they are less stable than their parent compounds. In fact, in the isolated selenoaldehydes, sterically bulky substituents are introduced to the carbon atoms that are close to the CSe groups .…”

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confidence: 99%

α-Hydroxy and α-Oxo Selenoamides: Synthesis via Nucleophilic Selenocarbamoylation of Carbonyl Compounds and Characterization

et al. 2015

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Carbonyl compounds were added to selenocarbamoyllithiums to generate α-hydroxy and α-oxo selenoamides. Their conformations were determined by X-ray analyses. These compounds adopted conformations that were almost identical to those of ordinary amides. Unlike the consistency of the chemical shifts of the C═Se groups of the selenoamides in (13)C NMR spectra and the (1)J coupling constants of the C═Se groups, the substituents far from the selenium atom influenced the chemical shifts in (77)Se NMR.

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confidence: 99%

α-Hydroxy and α-Oxo Selenoamides: Synthesis via Nucleophilic Selenocarbamoylation of Carbonyl Compounds and Characterization

et al. 2015

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“…In order to stabilize these substances, bulky substituents are typically incorporated at the selenocarbonyl group . Although being dependent on their exact nature, heteroatom-containing functional groups, such as amino, alkoxy, sulfenyl, and selenenyl groups, introduced at the selenocarbonyl carbon also bring about stabilization of these compounds . As a result, selenoamides, selenoic acid O -esters, and their sulfur and selenium counterparts , have been widely studied.…”

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(Selenocarbamoyl)silanes and -germanes: Their Synthesis Using (Selenocarbamoyl)lithium and Characterization

et al. 2010

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Twofold Extrusion Reactions

Guziec

2012

Organic Reactions

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Twofold extrusion reactions are chemical transformations in which two small inorganic molecules or atoms connecting carbon or nitrogen atoms are lost, generating the corresponding carbon‐carbon or carbon‐nitrogen double bonds. These reactions are particularly useful for the preparation of sterically hindered alkenes and imines. The inorganic species liberated in twofold extrusion reactions can be molecular nitrogen, sulfur, selenium, tellurium, sulfur dioxide, sulfur monoxide, carbon dioxide or carbon monoxide. The most common precursors for twofold extrusion reactions are 1,3,4‐thiadiazolines, which thermally extrude molecular nitrogen affording thiiranes. These thiiranes can be readily desulfurized to afford the corresponding alkenes using tertiary phosphines. The corresponding 1,3,4‐selenadiazolines thermally extrude both molecular nitrogen and atomic selenium directly affording alkenes. Alkenes can also be prepared by formal extrusions of molecular nitrogen plus sulfur dioxide or sulfur monoxide. Extremely sterically hindered imines can be prepared by extrusions of molecular nitrogen and sulfur or selenium from in situ generated heterocyclic precursors. Other less common twofold extrusion reactions are also reported. The detailed preparations of the required precursors for the twofold extrusion reactions as well as the mechanisms of these extrusion processes are discussed in this chapter. The utility of twofold extrusion reactions in the preparations of ‘molecular rotors’ and other extremely sterically hindered alkenes is presented. The steric limitations of the twofold extrusion reactions are discussed along with comparisons of these reactions with other alkene‐ and imine‐forming synthetic methods. The Tabular Survey covers material through the end of 2009.

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Seleno- and Telluroaldehydes and -ketones

Cited by 6 publications

References 668 publications

α-Hydroxy and α-Oxo Selenoamides: Synthesis via Nucleophilic Selenocarbamoylation of Carbonyl Compounds and Characterization

α-Hydroxy and α-Oxo Selenoamides: Synthesis via Nucleophilic Selenocarbamoylation of Carbonyl Compounds and Characterization

(Selenocarbamoyl)silanes and -germanes: Their Synthesis Using (Selenocarbamoyl)lithium and Characterization

Twofold Extrusion Reactions

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