New and Convenient Synthesis of Lithiated Allenes and Ketenimines Based on Readily Available Aryl-Substituted Ketones and Amides

Seyferth, Dietmar; Langer, Peter; Doering, Manfred

doi:10.1021/om00010a006

Cited by 22 publications

(17 citation statements)

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“…in a reaction recently developed by us. [11,12] This reaction proceeds by lithiation of the silyl enol ether, elimination of lithium silanolate and lithiation of 1,1-diphenylallene (Scheme 2). The elimination either occurs directly (path A) or proceeds through a OǞC silyl migration/Peterson elimination sequence (path B).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nitrile Oligomers through Multiple Anion Capture Reactions of Allene Dianions

Langer

Döring²,

Seyferth

et al. 2003

Eur J Org Chem

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Domino reactions between 1,1‐dilithio‐3,3‐diphenylallene and nitriles resulted in the formation of products containing up to four nitrile molecules, representing the highest number to date of nitrile molecules involved in the formation of unambiguously characterized oligomers. The unusual domino process reported constitutes a new method for the synthesis of imidazoles. The solid‐state structures of the sterically encumbered products were studied by crystal structure analyses. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Resultsmentioning

confidence: 99%

Synthesis of Nitrile Oligomers through Multiple Anion Capture Reactions of Allene Dianions

Langer

Döring²,

Seyferth

et al. 2003

Eur J Org Chem

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“…Reagents: i, n-BuLi (2 equiv), THF, -78ºC; ii, Ph2PCl (2 equiv), -78ºC. [29]. It is noteworthy the reaction of dianion 42 with an excess of benzonitrile leading to cyclization products 44 and 45 [30], with incorporation of up to 4 nitrile molecules in the case of 45 (Scheme 11).…”

Section: Methodsmentioning

confidence: 99%

Organodilithium Intermediates as Useful Dianionic Synthons: Recent Advances

Foubelo¹,

Yus

2005

COC

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“…5 1,1-Diphenyl-3,3-dilithioallene 2 was generated in one pot by treatment of the TBDMS enol ether 1 with an excess of LDA in THF, a reaction recently developed by us. 6 This process presumably proceeds via a mechanism involving initial lithiation of the allyl system of the silyl enol ether, elimination of lithium silanolate and lithiation of the 1,1-diphenylallene formed (Scheme 1). The elimination could either occur directly (path A) or proceed via a O?C silyl migration/Peterson elimination sequence (path B).…”

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confidence: 99%