Novel Cycloaddition of Nitriles with Monolithio- and Dilithiobutadienes

Chen, Jinglong; Song, Qiuling; Wang, Congyang; Xi, Zhenfeng

doi:10.1021/ja0262176

Cited by 70 publications

(55 citation statements)

References 11 publications

(7 reference statements)

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“…Surprisingly, the same products can be obtained when 1-lithio-1,3-dienes are used [49]. These results are very different from the usual reaction between organolithium and nitriles as shown in standard textbooks where ketones or imines are formed.…”

Section: 4 14-bimetallic Compoundscontrasting

confidence: 52%

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Shimeng

et al. 2011

Chin. Sci. Bull.

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Organometallics are a family of useful organic chemicals because they play important roles in organic synthesis as reagents and as catalysts. They can be classified according to the number of metals they contain. Bimetallic compounds are important organometallics and they are either homobimetallic or heterobimetallic depending on whether the two metals are the same or different. In this paper, we focus on homobimetallic compounds. Homobimetallic compounds are generally used as dianions to react with electrophiles in organic synthesis. Recently, homobimetallics have also been used as catalysts in organic reactions such as in asymmetric reactions. homobimetallics, reagent, catalyst, synthesis, application Citation:Wu W, Gu D L, Wang S M, et al. Recent developments in homobimetallic reagents and catalysts for organic synthesis.

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Section: 4 14-bimetallic Compoundscontrasting

confidence: 52%

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Shimeng

et al. 2011

Chin. Sci. Bull.

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“…Since we initially noticed the novel reaction patterns of 1,4-dilithio-1,3-diene derivatives 5 in 2000, 6 we have been investigating the reactions of 5 with various organic substrates. [6][7][8][9][10][11] In order to study on the reaction of the addition intermediates 1 or 2 with nucleophiles, we used 5 as model compounds, expecting that selectivity can be improved and new types of reaction patterns can be discovered. 5 As demonstrated in Scheme 3, both carbophilic addition intermediates 6 (Scheme 3, type a) and thiophilic addition intermediates 7 (Scheme 3, type b) can be expected as the first intermediate compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Our recent studies have demonstrated that 1-lithiobutadiene derivatives 13 react with various organic substrates in a very much different manner from those of normal organolithium reagents. 10,12 Thus, the reaction of 1-lithiobutadienes 13 with CS 2 also interested us. As demonstrated in Scheme 4, the first addition intermediates may be carbophilic addition compound 14 and/or thiophilic addition compound 15.…”

mentioning

confidence: 99%

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

Wang¹,

Chen²,

Song³

et al. 2003

Arkivoc

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Dedicated to Professor Zhitang AbstractBoth carbophilic addition and thiophilic addition were involved in the first step intermolecular reaction of 1,4-dilithio-1,3-diene derivatives with carbon disulfide. Thus in situ generated carbophilic addition intermediates and thiophilic addition intermediates underwent a second step intramolecular carbophilic and thiophilic additions. Multiply substituted thiophenes were isolated as the results of cleavage of the C=S double bonds, while thiopyran-2-thiones were produced via cycloaddition reactions. In addition to 1,4-dilithio-1,3-dienes, monolithio reagents also showed interesting reactions with carbon disulfide. Thiophenes were also generated in the reaction of 1-lithio-1,3-dienes with carbon disulfide.

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“…19). 34,35 Depending on the substitution patterns of the butadienyl skeletons, substituted pyridines, pyrroles, and/or linear butadienyl imines were formed in good to excellent yields. The N-lithioketimines 21 must be formed as the reactive addition intermediates at À78 C, because hydrolysis of the reaction mixture at À78…”

Section: Cycloaddition Reaction With Organonitriles: Preparation Of Mmentioning

confidence: 99%

1-Lithio-1,3-dienes: Useful Building Blocks for Cyclic Compounds

2007

Bulletin of the Chemical Society of Japan

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In this account, our recent results on the application of substituted 1-lithio-1,3-dienes as building blocks for the preparation of a wide variety of cyclic compounds and linear compounds are briefly summarized. Results have revealed that the essential factor which makes 1-lithio-1,3-diene derivatives useful and unique as building blocks is the intracooperation between the alkenyllithium moiety and the butadienyl skeleton, notwithstanding that the alkenyllithium moiety itself reacts with organic substrates in the usual way. In addition, the substitution patterns and the nature of the substituents on the butadienyl skeleton have been demonstrated to affect remarkably the reaction pathways of 1-lithio-1,3-diene derivatives.

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Novel Cycloaddition of Nitriles with Monolithio- and Dilithiobutadienes

Cited by 70 publications

References 11 publications

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Recent developments in homobimetallic reagents and catalysts for organic synthesis

Preparation of S-containing heterocycles via novel reaction patterns of carbon disulfide with 1-lithiobutadienes and 1,4-dilithiobutadienes

1-Lithio-1,3-dienes: Useful Building Blocks for Cyclic Compounds

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