Synthesis of Stannole Anion by Alkylation of Stannole Dianion

Saito, Masaichi; Haga, Ryuta; Yoshioka, Michikazu

doi:10.1246/cl.2003.912

Cited by 38 publications

(18 citation statements)

References 22 publications

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“…Tbt-substituted trihalostannane was synthesized by the reaction of SnCl 4 with TbtLi. Tbt-and Dip-substituted stannane, Tbt(Dip)SnH 2 (3), was prepared by the nucleophilic displacement reaction of the Tbt-substituted trihalostannane using DipMgBr, followed by reduction with LiAlH 4 . Bromination reaction of 3 using Br 2 in ether afforded the corresponding dibromostannane 4.…”

Section: Resultsmentioning

confidence: 99%

“…Saito and his co-workers have recently reported the spectroscopic observation of a stannole dianion. [3] Although Schmidt et al have proposed the formation of (C 6 H 5 ) 2 SnLi 2 in the reaction of (C 6 H 5 ) 2 SnCl 2 with 4 molar amounts of Li, [4,5] the yields of the trapping reactions are not high and the generation of dilithiodiphenylstannane was not evidenced by 119 Sn and 7 Li NMR spectroscopy. More recently, Egorov et al reported the 119 Sn and 13 C NMR studies of Et 2 SnLi 2 and (C 6 H 5 ) 2 SnLi 2 .…”

Section: Introductionmentioning

confidence: 99%

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Generation and Reactions of Overcrowded Diaryldilithiostannane and Diaryldipotassiostannane

et al. 2005

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Exhaustive reduction of an overcrowded dibromostannane bearing two bulky aromatic substituents, Tbt(Dip)SnBr2 {Tbt = 2,4,6‐tris[bis(trimethylsilyl)methyl]phenyl; Dip = 2,6‐diisopropylphenyl}, with an excess amount of lithium naphthalenide in THF at –78 °C gave the corresponding dilithiostannane, Tbt(Dip)SnLi2, the generation of which was confirmed by trapping experiments with some electrophiles together with 119Sn and 7Li NMR spectroscopy. The diaryldilithiostannane was found to be stable in solution under an inert gas below –25 °C. The potassium analogue, Tbt(Dip)SnK2, was also generated by the reduction of the dibromostannane in THF at –78 °C by the use of KC8 as a reductant. The reactions of dilithiostannane and dipotassiostannane obtained with o‐dibromobenzene did not give a stannacyclopropabenzene derivative but an unexpected cyclization product, a stannacyclobutabenzene derivative, in contrast to thereactions of the corresponding dilithiosilane and dilithiogermane, Tbt(Dip)ELi2 (E = Si, Ge), with o‐dibromobenzene leading to the formation of the corresponding metallacyclopropabenzenes as stable crystalline compounds. A preliminary result of the synthesis of a tin–tellurium double‐bond compound from the dilithiostannane is also presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Generation and Reactions of Overcrowded Diaryldilithiostannane and Diaryldipotassiostannane

et al. 2005

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“…[19] When 1 equiv. of tert-butyl chloride was added to a diethyl ether solution of the stannole dianion 3, the color of the reaction mixture changed from deep red to bright red.…”

Section: Alkylation Of Stannole Dianionmentioning

confidence: 99%

“…of tert-butyl chloride was added to a diethyl ether solution of the stannole dianion 3, the color of the reaction mixture changed from deep red to bright red. By treatment of the reaction mixture with methyl iodide, the 1-tert-butyl-1-methylstannole 15 [19] was obtained in 55 % yield, suggesting the formation of the stannole anion 16 bearing a tertbutyl group on the tin atom (Scheme 7). The formation of 16 from 3 is reasonably explained by an electron-transfer mechanism, as observed in the reaction of the tributylstannyl anion with tert-butyl halides.…”

Section: Alkylation Of Stannole Dianionmentioning

confidence: 99%

Synthesis and Reactions of Stannole Anions

2007

Self Cite

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The synthesis of stannole anions bearing various substituents on the tin atom is described. The reduction of hexaphenylstannole by the proper amount of lithium gave 1,2,3,4,5‐pentaphenylstannole anion 1. The reaction of 1 with 1,n‐dihaloalkanes (n = 1, 3, 4, 5, 6) gave the corresponding 1,n‐bis(1‐stannacyclopentadien‐1‐yl)alkanes. In contrast, the reaction of 1 with 1,2‐dihaloalkanes gave the 1,1′‐bistannole. The reactions of stannole dianion 3 with an equimolar amount of bulky alkyl, aryl, silyl, and stannyl halides gave the corresponding stannole anions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…The chemistry of group 14 metallole dianions has been developed enormously [11,12], and recently the stannole dianion [SnC 4 Ph 4 ] 2− was also reported [13,14,15,16]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis and NMR-Study of the 2,3,4,5-Tetraethylsilole Dianion [SiC4Et4]2−•2[Li]+

Hong

2011

Molecules

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The previously unknown silole dianion [SiC4Et4]2−•2[Li]+ (3) was prepared by the sonication of 1,1-dichloro-2,3,4,5-tetraethyl-1-silacyclopentadiene [Cl2SiC4Et4, 2] with more than four equivalent of lithium in THF. 1H-, 13C-, and 29Si-NMR data of 3 are compared with those of the reported silole dianion [SiC4Ph4]2−. Trapping of 3 with trimethylchlorosilane gave 1,1-bis(trimethylsilyl)-2,3,4,5-tetraethyl-1-silacyclopentadiene [(Me3Si)2SiC4Et4, 4] in high yield. The silole of 2 was synthesized in high yield in three steps by a modified procedure using Cp2ZrCl2 via Cp2ZrC4Et4 and 1,4-dibromo-1,2,3,4-tetraethyl-1,3-butadiene.

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Synthesis of Stannole Anion by Alkylation of Stannole Dianion

Cited by 38 publications

References 22 publications

Generation and Reactions of Overcrowded Diaryldilithiostannane and Diaryldipotassiostannane

Generation and Reactions of Overcrowded Diaryldilithiostannane and Diaryldipotassiostannane

Synthesis and Reactions of Stannole Anions

Synthesis and NMR-Study of the 2,3,4,5-Tetraethylsilole Dianion [SiC4Et4]2−•2[Li]+

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