Cyclic organolead compounds

Beelen, D.C. van; Wolters, J.

doi:10.1016/s0022-328x(00)90002-0

Cited by 2 publications

(2 citation statements)

References 11 publications

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“…The latter was synthesised according to a published procedure [37]. 1 H NMR (in CDCL): 5H(CH 2 ) 3.13 ppm ( 4 J( 207 Pb-1 H) 11 Hz). It appeared to be contaminated with 1,2-diphenylethane, which resulted from the hydrolysis of the di-Grignard compound.…”

Section: Synthesis Of 55-diphenyi-1011-dihydro-5-h-dibenzo[bf]plummentioning

confidence: 99%

“…Although 10,10-dimethylphenoxaplumbin in which Ε denotes an oxygen atom, could be synthesised from bis-(o-lithiophenyl)ether and the appropriate diorganolead dibromide [1], it was not possible to synthesise the corresponding diphenyl compound in this way. In the field of phenoxastannin derivatives the same phenomenon was observed.…”

Section: Synthesis Of 55-diphenyi-1011-dihydro-5-h-dibenzo[bf]plummentioning

confidence: 99%

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Synthesis and Multinuclear NMR Properties of Sixmembered Heterocyclic Organolead Compounds

Beelen¹,

Rijn²,

Heringa³

et al. 1997

Main Group Metal Chemistry

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Several six-membered heterocyclic organolead compounds were synthesized from the appropriate di-Grignard resp. organodilithio compounds and a (diorgano)lead dihalide. The compounds were investigated by multinuclear NMR spectroscopy. Variable temperature 1 H NMR measurements revealed a conformational equilibrium. In the 13 C and 207 Pb NMR spectra specific effects caused by the presence of a lead atom in the ring system could be observed. IntroductionIn several previous studies we had investigated some aspects of the chemistry of cyclic organolead compounds, including five-membered ring compounds, in particular [2,3]. Subsequently we studied several six-membered cyclic organolead compounds of the general type (1) and the results are presented here. We were particularly interested in the effects of variation of the element Ε on the multinuclear NMR properties. Results on 10,10-dimethylphenoxaplumbin, in which Ε denotes an oxygen atom and R is CH 3 , have been previously published [1]. Materials and Methods1 H and 13 C NMR spectra were recorded on a JEOL-PFT-100 NMR spectrometer. 207 Pb NMR spectra were recorded on a Bruker WH 90 multinuclear spectrometer. Experimental details on the recording and assignments of the various spectra have been published elsewhere [24,36]. All synthetic reactions were carried out under dry nitrogen. The solvents diethylether (ether) and tetrahydrofuran (THF) were distilled from lithiumaluminiumhydride before use. For more experimental details see ref.[39]. Synthesis of bis-(o-bromophenyl)methane [6]A solution of 25.0 g of o-dibromobenzene (0.106 mol) and 19.9 g of 1,2-dibromoethane (0.106 mol) in 125 ml of ether was added dropwise to 5.15 g of magnesium (0.212 mol) in 15 ml of ether which was stirred magnetically. External cooling was applied by means of an ice bath and the reagents were added at such a rate that the temperature of the reaction mixture did not exceed 10°C. After the reaction was completed (ca. 3 h) the mixture was stirred for another 10 min. and at 0°C 19.7 g of o-bromobenzaldehyde (0.106 mol) was added dropwise. After refluxing for 2 h the mixture was cooled down to room temperature and hydrolysed with an aqueous ammonium chloride solution. The ether layer was isolated and the water layer was extracted with a 100 ml portion of ether. The combined ether fractions were dried over anhydrous magnesium sulfate. After filtration and evaporation, a yellow oil of 2,2'-dibromodiphenylmethanol was obtained. ©Part III, see ref.[1] Abstract R' R (1) 37 Brought to you by | Purdue University Libraries

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Section: Synthesis Of 55-diphenyi-1011-dihydro-5-h-dibenzo[bf]plummentioning

confidence: 99%

Section: Synthesis Of 55-diphenyi-1011-dihydro-5-h-dibenzo[bf]plummentioning

confidence: 99%

Synthesis and Multinuclear NMR Properties of Sixmembered Heterocyclic Organolead Compounds

Beelen¹,

Rijn²,

Heringa³

et al. 1997

Main Group Metal Chemistry

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ChemInform Abstract: CYCLIC ORGANOLEAD COMPOUNDS. III. SYNTHESIS AND DYNAMIC BEHAVIOR OF 10,10‐DIMETHYLPHENOXAPLUMBIN AND A TWELVE MEMBERED HETEROCYCLIC ORGANOLEAD COMPOUND C28H28O2PB2

Beelen¹,

Wolters²

1980

Chemischer Informationsdienst

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Cyclic organolead compounds

Cited by 2 publications

References 11 publications

Synthesis and Multinuclear NMR Properties of Sixmembered Heterocyclic Organolead Compounds

Synthesis and Multinuclear NMR Properties of Sixmembered Heterocyclic Organolead Compounds

ChemInform Abstract: CYCLIC ORGANOLEAD COMPOUNDS. III. SYNTHESIS AND DYNAMIC BEHAVIOR OF 10,10‐DIMETHYLPHENOXAPLUMBIN AND A TWELVE MEMBERED HETEROCYCLIC ORGANOLEAD COMPOUND C28H28O2PB2

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