UnexpectedFormation of 3-Methylsulfanyl-2-phenyl-2-cyclobutenone in the Reaction of 1'3-Dilithio-2-propynylbenzene with Methoxymethyl Isothiocyanate

Тарасова, О. А.; Brandsma, L.; Nedolya, N. А.; Ushakov, Igor А.; Dmitrieva, G. V.; Коротеева, Т. В.

doi:10.1023/b:rujo.0000034923.10292.65

Cited by 6 publications

(3 citation statements)

References 2 publications

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“…Our study was continued by applying 3-phenyl-1-propyne ( 8 ) as a substrate under the same conditions (Scheme ). It is known that 8 produces 1,3-dilithio-3-phenylpropyne ( 9 ) in the presence of 2.0 equiv of n -butyllithium (Scheme a). − As expected, by addition of a solution of 9 to a solution of 2.0 equiv of IPrAuCl in THF under an argon atmosphere, a dinuclear propargylic NHC gold(I) complex ( 10 ) was obtained (Scheme b).…”

Section: Results and Discussionmentioning

confidence: 61%

Dinuclear NHC Gold(I) Allenyl and Propargyl Complexes: An Experimental and Theoretical Study

et al. 2019

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The synthesis and isolation of the dinuclear NHC gold(I) allene-1,3-diyl complex Ph(IPrAu)CCCH(AuIPr) and the dinuclear NHC gold(I) propyne-1,3-diyl complex Ph(IPrAu)CH−CC−Au(IPr) are presented. The monoprotodeauration reactions of these dinuclear complexes selectively led to the mononuclear organogold complexes Ph(IPrAu)CCCH 2 and PhCH 2 −CC− Au(IPr), respectively. The experimental structures and the obtained analytical data of the synthesized complexes as well as the results of a computational DFT study of their thermodynamic stability are compared systematically.

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Section: Results and Discussionmentioning

confidence: 61%

Dinuclear NHC Gold(I) Allenyl and Propargyl Complexes: An Experimental and Theoretical Study

et al. 2019

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“…1,3-Dilithiopropynes with other substituents including aryl, alkylsulfanyl, etc. could also be prepared and exhibited similar reactivity …”

Section: 2- and 13-dicarbanion Compoundsmentioning

confidence: 99%

Dicarbanion Compounds: The Bridge between Organometallic Reagents and Mononuclear Heterocycles

Chai

Zhang

2022

Organometallics

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Dicarbanion compounds, namely organo-bi-metallics in which two metal atoms are separated by all-carbon backbones, are of great importance in organometallic chemistry for not only the interest in the structure but also the wide application in synthesis, especially of mononuclear heterocycles. The synthetic methods and reactivities of dicarbanion compounds highly depend on the type of metals as well as the structure of backbones. For metal types, while there are examples of other metals, lithium and magnesium play important roles in the chemistry of dicarbanion compounds. For the backbone structure, different unsaturated bonds in the backbones result in different rigidities and orientations of carbon−metal bonds and thus have a great impact on the reactivity of dicarbanion compounds. Herein, a general review of the preparation, structure, and reactivity of dicarbanion compounds with different metals and backbones are presented, mainly focusing on the dicarbanion compounds that have been or may potentially be employed in mononuclear heterocycle synthesis. Heterocycles mentioned in this review are mostly metallacycles because of the limitation of synthetic methods.

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“…The treatment of propargylbenzene (558) with butyllithium generated 1,3-dilithiopropargylbenzene (559), which underwent a nucleophilic addition to isothiocyanates 560 followed by protonation, isomerization, intramolecular nucleophilic addition, and methylation, affording 2-iminothietane derivatives 564 [159,160] (Scheme 128).…”

Section: Synthesis Via Nucleophilic Additionmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

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UnexpectedFormation of 3-Methylsulfanyl-2-phenyl-2-cyclobutenone in the Reaction of 1'3-Dilithio-2-propynylbenzene with Methoxymethyl Isothiocyanate

Cited by 6 publications

References 2 publications

Dinuclear NHC Gold(I) Allenyl and Propargyl Complexes: An Experimental and Theoretical Study

Dinuclear NHC Gold(I) Allenyl and Propargyl Complexes: An Experimental and Theoretical Study

Dicarbanion Compounds: The Bridge between Organometallic Reagents and Mononuclear Heterocycles

Recent synthesis of thietanes

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