APPLICATION OF BIS(<i>p</i>-METHOXYPHENYL)SELENOXIDE AS AN OXIDIZING AGENT OF KORNBLUM OXIDATION

Ariyoshi, Kimio; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio

doi:10.1246/cl.1984.891

Cited by 21 publications

(3 citation statements)

References 7 publications

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“…The compound 2 is an attractive starting material for the synthesis of various important pharmaceuticals. However, there have been few direct, practical synthetic methods so far despite their synthetic importance . Of the various indirect procedures, the hydrolysis of α,α,α‘,α‘-tetrabromo- o - xylene is thought to be the best method, although α,α,α‘,α‘-tetrabromo- o -xylene must be prepared independently by bromination of o -xylene using excess bromine.…”

Section: Resultsmentioning

confidence: 99%

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

1999

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An approach for partial oxygenation through a carbocation as an intermediate was successfully developed by using nitric oxide under the influence of N-hydroxyphthalimide. Thus, a variety of benzylic ethers were converted into the corresponding partially oxidized compounds, which are difficult to prepare by conventional methods, in high yields. For example, the reaction of phthalane with NO in the presence of a catalytic amount of NHPI at 60 degrees C gave phthalaldehyde in 80% yield. The reaction was found to proceed through the formation of a hemiacetal, such as 1-hydroxyphthalane. In addition, 1,3-di-tert-butoxymethyl benzene afforded 1,3-benzenedicarbaldehyde in good yield. On the other hand, isochroman was converted into 1,1'-oxodiisochromane under these reaction conditions. The reaction of ethers with NO in the presence of a NHPI catalyst is thought to proceed via the formation of a carbocation as an intermediate. A possible reaction path was suggested.

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Section: Resultsmentioning

confidence: 99%

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

1999

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“…The most important types of synthetic organoselenium compounds are diorganodiselenides (R-Se-Se-R) [175,176], selenols (R-Se-H) [177], diorganoselenides (R-Se-R ) [178,179], diorganoselenoxides (R 2 Se = O) [180][181][182], selenenyl sulfides (R-Se-S-R ) [183], organoselenium halides (R-Se-X, R 2 SeX 2 and R 3 SeX) [184], selenenic and selenonic acids (R-Se-OH, R-Se(O)-OH, R-Se(O) 2 )-OH) [185], and selenic and selenious acid aliphatic and aromatic and cyclic esters (alkyl and aryl selenates and selenites). In the last 20 years a great effort has been directed toward the synthesis of biologically active organoselenium compounds as potential antitumor agents [20,21,25,[186][187][188][189][190][191], enzyme modulators [192], antioxidants [193][194][195], antimicrobials [196][197][198][199][200][201][202], antivirals [203][204][205][206][207][208][209], and cytokine inducers [210].…”

Section: Organoselenium Natural and Synthetic Compoundsmentioning

confidence: 99%

Selenium-Containing Polysaccharides—Structural Diversity, Biosynthesis, Chemical Modifications and Biological Activity

2021

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Selenosugars are a group of sugar derivatives of great structural diversity (e.g., molar masses, selenium oxidation state, and selenium binding), obtained as a result of biosynthesis, chemical modification of natural compounds, or chemical synthesis. Seleno-monosaccharides and disaccharides are known to be non-toxic products of the natural metabolism of selenium compounds in mammals. In the case of the selenium-containing polysaccharides of natural origin, their formation is also postulated as a form of detoxification of excess selenium in microorganisms, mushroom, and plants. The valency of selenium in selenium-containing polysaccharides can be: 0 (encapsulated nano-selenium), IV (selenites of polysaccharides), or II (selenoglycosides or selenium built into the sugar ring to replace oxygen). The great interest in Se-polysaccharides results from the expected synergy between selenium and polysaccharides. Several plant- and mushroom-derived polysaccharides are potent macromolecules with antitumor, immunomodulatory, antioxidant, and other biological properties. Selenium, a trace element of fundamental importance to human health, has been shown to possess several analogous functions. The mechanism by which selenium exerts anticancer and immunomodulatory activity differs from that of polysaccharide fractions, but a similar pharmacological effect suggests a possible synergy of these two agents. Various functions of Se-polysaccharides have been explored, including antitumor, immune-enhancement, antioxidant, antidiabetic, anti-inflammatory, hepatoprotective, and neuroprotective activities. Due to being non-toxic or much less toxic than inorganic selenium compounds, Se-polysaccharides are potential dietary supplements that could be used, e.g., in chemoprevention.

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“…Representative examples of the reaction are shown in equations (16)- (20). There is an interesting limitation to the method: 4-nitrobenzyl chloride gives only 1% of the aldehyde, the major product being the result of single-electron transfer and radical coupling (equation 21).42 A PdQ catalyst has been used in situ to isomerize a secondary allylic halide prior to oxidation (equation 22). There appear to be no examples of the oxidation of secondary halides to ketones by this method, presumably for reasons of lower reactivity.…”

Section: The Hass-bender Reactionmentioning

confidence: 99%

Oxidation of Carbon–Halogen Bonds

Kilenyi

1991

Comprehensive Organic Synthesis

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APPLICATION OF BIS(p-METHOXYPHENYL)SELENOXIDE AS AN OXIDIZING AGENT OF KORNBLUM OXIDATION

Abstract: The title selenoxide was found to serve as a suitable agent for Kornblum oxidations of various benzyl bromides to the corresponding carbonyl compounds. On the other hand, the analogous sulfoxide and telluroxide hardly promoted such oxidations.

Cited by 21 publications

References 7 publications

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

Selenium-Containing Polysaccharides—Structural Diversity, Biosynthesis, Chemical Modifications and Biological Activity

Oxidation of Carbon–Halogen Bonds

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