Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data

Dubac, J.; Laporterie, A.; Manuel, Georges

doi:10.1021/cr00099a008

Cited by 287 publications

(171 citation statements)

References 64 publications

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“…In addition to the well known reactivity of the cyclic diene system of metalloles [1,16] the presence of the diethylboryl group in the 3-position of the stannoles 2 opens the way to further attractive transformations. Thus, any reagent containing a nucleophilic centre will be attracted by the electrophilic boron atom.…”

Section: Reactions Of the Stannoles 2 With Isocyanatesmentioning

confidence: 99%

Reactions of 3‐(Diethylboryl)stannoles with Isocyanates

2009

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Diethynyl(diphenyl)stannane was prepared, fully characterised in solution and in the solid state, and its reaction with triethylborane, BEt3, afforded 3‐(diethylboryl)‐4‐ethyl‐1,1‐diphenyl‐stannole in essentially quantitative yield. Treatment with isocyanates converted this stannole and the known analogous 1,1‐dimethyl derivative into novel bicyclic compounds containing an aminoborane unit. These reactions were found to proceed diastereoselectively, again in essentially quantitative yield. The bicyclic compounds react with methanol through rearrangement and elimination of ethyl(dimethoxy)borane to give novel 1‐stannacyclopent‐3‐ene derivatives, one of which could be structurally characterised by X‐ray analysis. All final products and intermediates were studied in solution by multinuclear NMR spectroscopy (1H, 11B, 13C, 119Sn NMR).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Reactions Of the Stannoles 2 With Isocyanatesmentioning

confidence: 99%

Reactions of 3‐(Diethylboryl)stannoles with Isocyanates

2009

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“…Group 14 metalloles, [1] or metallacyclopentadienes, have attracted much attention because of interest in them as a possible precursor for the preparation of conjugated polymers having unique electronic structures [2,3] as well as the potential aromaticity of their anions. [4] Since the successful synthesis of some oligo(1,1-silole)s [5,6] and poly(1,1-silole)s, they have been applied to organic electroluminescent (EL) devices.…”

Section: Introductionmentioning

confidence: 99%

“…[9] In contrast to the silicon and germanium analogs, however, attempts to prepare oligo-and poly(1,1-stannole)s are still unknown. Although the synthesis and some simple reactions of stannoles have been reviewed, [1] even the synthesis of bi (1,1-stannole) has not yet been successful.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structures of Bi(1,1‐stannole)s

2005

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The synthesis and structures of bi(1,1‐stannole)s are described. Treatment of 1‐bromo‐4‐(dibromophenylstannyl)‐1,3‐butadiene with tert‐butyllithium gives the bi(1,1‐stannole) having a phenyl group on each tin atom, whereas treatment of 1‐bromo‐4‐(tribromostannyl)‐1,3‐butadiene with phenyl‐ or bulky alkyllithiums gives the bi(1,1‐stannole) having a phenyl or an alkyl group on each tin atom. The X‐ray analysis of the tert‐butyl‐substituted bi(1,1‐stannole) is also described. All bi(1,1‐stannole)s display two shoulder absorption bands due to π–π* and σ–π* transitions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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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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Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data

Cited by 287 publications

References 64 publications

Reactions of 3‐(Diethylboryl)stannoles with Isocyanates

Reactions of 3‐(Diethylboryl)stannoles with Isocyanates

Synthesis and Structures of Bi(1,1‐stannole)s

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

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