Reaction of an ammonium eneselenolate derived from a selenothioacetic acid <i>S</i>‐ester with electron‐deficient alkenes and alkynes

Murai, Toshiaki; Kondo, Taichi; Katō, Shinzi

doi:10.1002/hc.20003

Cited by 4 publications

(3 citation statements)

References 21 publications

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“…38 These results are markedly different from those arising from studies of the reaction of 5b with electron-deficient alkynes in the presence of Et 3 N (see Scheme 16). Finally, reactions of ammonium eneselenolate 83 with a,b-unsaturated ketones not only produce the expected Michael adducts 86 but they also generate product (e.g., 87) in which two molecules of a a,b-unsaturated ketone is incorporated (Scheme 44).…”

Section: Scheme 41contrasting

confidence: 53%

“…The in situ generated ammonium eneselenolate 83 is observed to react with electron-deficient alkynes to form divinyl selenides 28 with high stereoselectivity regardless of the substitution pattern adjacent to the carbonyl group (Scheme 43). 38 These results are markedly different from those arising from studies of the reaction of 5b with electron-deficient alkynes in the presence of Et 3 N (see Scheme 16). Finally, reactions of ammonium eneselenolate 83 with a,b-unsaturated ketones not only produce the expected Michael adducts 86 but they also generate product (e.g., 87) in which two molecules of a a,b-unsaturated ketone is incorporated (Scheme 44).…”

Section: Scheme 42mentioning

confidence: 73%

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Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Murai¹

2005

Synlett

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This review describes the synthesis and reactions of selenothioic acid S-esters and diselenoic acid esters. Synthetic work with these substances has provided observations, which have led to a proposal about factors that effect their stability. A survey shows that aliphatic derivatives of selenothioic acid S-esters, although being stable compounds, are highly reactive with various electrophilic and nucleophilic reagents. In addition, a-protons in these esters have high acidities. Studies have shown that the chemistry of these esters can be utilized in the synthesis of new types of organoselenium compounds.

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Section: Scheme 41contrasting

confidence: 53%

Section: Scheme 42mentioning

confidence: 73%

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Murai¹

2005

Synlett

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“…Although a number of methods have been developed for the synthesis of vinyl selenides,19, 20 the synthesis of divinyl selenides is much less investigated 21–27. Furthermore, although the addition of electrophilic selenium species to olefinic systems has been the subject of many studies,28–30 the additions to acetylenic systems have received much less attention 18, 19, 31–36.…”

Section: Resultsmentioning

confidence: 99%

Reaction of selenium and tellurium halides with propargyl alcohols. The regio‐ and stereoselectivity of addition to the triple bond

Braverman

Cherkinsky

Jana

et al. 2010

J of Physical Organic Chem

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A convenient method to incorporate selenium into an organic molecule is reported. Various aspects of the reaction of SeCl2 with propargyl alcohols, i.e., identity of reacting functionality, regiospecificity, and stereospecificity, differ from expectations based on known reactions of these alcohols with SCl2. Selenium dihalides undergo smooth 1,2‐addition to the triple bond of various propargylic alcohols resulting in the formation of the corresponding functionalized divinyl selenides in high yields and with complete regio‐ and stereospecificity. Of special mechanistic interest is the syn‐addition and anti‐Markovnikov orientation observed in all cases. Copyright © 2010 John Wiley & Sons, Ltd.

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NMR of Organoselenium and Organotellurium Compounds

Panda

Singh

2012

Patai's Chemistry of Functional Groups

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This chapter gives a systematic account of and surveys the available data on 77 Se and 125 Te NMR spectra of organochalcogen compounds such as chacogenols, mono and dichalcogenides, chalcogenolates, tetra and hexa substituted chalcogen compounds, chalcogenyl halides, chalcogen‐containing heterocycles and macrocycles, chalcogen‐oxygen/nitrogen compounds, etc. The review is based on the literature from 1985 to 2011 and includes 780 references. The 77 Se/ 125 Te NMR spectra of organochalcogen compounds reveal expansive chemical shifts (δ Se /δ Te ) leading to sharp sensitivity of these nuclei (Se/Te) to their environment such as solvent, temperature, molecular geometry, ligand backbone, oxidation state, chelate ring size, steric strain, etc. This is well illustrated by the advantageous use of this spectroscopy in the successful determination of the solution state structure of several organochalcogen compounds. It is noted that the 125 Te and 77 Se chemical shifts of a large number of structurally similar organotellurium and selenium compounds show linear relationship.

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Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S‐ester with electron‐deficient alkenes and alkynes

Cited by 4 publications

References 21 publications

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Reaction of selenium and tellurium halides with propargyl alcohols. The regio‐ and stereoselectivity of addition to the triple bond

NMR of Organoselenium and Organotellurium Compounds

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