Organometallic bis(p-hydroxyphenyl) derivatives of group IV elements and related compounds

Davidsohn, Wenzel E.; Laliberte, Bernard R.; Goddard, Charles M.; Henry, Malcolm C.

doi:10.1016/s0022-328x(00)80676-2

Cited by 45 publications

(18 citation statements)

References 14 publications

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“…The basic synthetic route for these derivatives was first reported by Davidsohn et al [3] and since it has been used for preparing several bisphenols (Fig. 3).…”

Section: Synthesis Of Bisphenols: Bis(4-hydroxyphenyl)r 1 R 2 -Silanementioning

confidence: 99%

“…Thus, it is possible to synthesize diphenols containing a carbon atom as central element, such as bis(phydroxyphenyl) dimethylmethane (BP-A) and some of its derivatives with several substitutions on the rings. [1] and (b) route proposed by Davidsohn et al [3] for derivatives containing germarylene or silarylene units. However, the procedure described by Mc Greal et al cannot be applied to the synthesis of derivatives containing silicon or germanium as central atom.…”

Section: Introductionmentioning

confidence: 99%

“…However, the procedure described by Mc Greal et al cannot be applied to the synthesis of derivatives containing silicon or germanium as central atom. For this reason, an alternative route was proposed by Davidsohn et al [3], where a dialkyl or diaryl-silane or -germane dihalide is added, at low temperature, to reaction product of p-bromophenol and n-BuLi (Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

“…Using this procedure, the preparation of bis(p-hydroxyphenyl)dimethyl-silane and germane [3 -7], bis(p-hydroxyphenyl)diphenyl-silane and -germane [3,5], bis(p-hydroxyphenyl)diethyl-silane [6,7] and germane [8], bis(p-hydroxyphenyl)di n propylsilane [6,7], bis(p-hydroxyphenyl)di n buthylgermane [8] and bis(p-hydroxyphenyl)methylphenylsilane [9] has been reported with good yield. Some structural variations upon these compounds have also been found following this route, for example, bis(o-hydroxyphenyl)diphenylsilane [10] and bis(2-methyl-p-hydroxyphenyl) dimethylsilane [11].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of new bi-functional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates)

Terraza

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et al. 2007

Designed Monomers and Polymers

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Abstract-Following the reaction route between a diphenol and phosgene/toluene solution in basic medium, six new bis(chloroformates) containing germarylene or silarylene units were synthesized with good yield. The variation on the structure is due to the nature of the groups bonded to the heteroatom. Therefore, combinations of Me, Et and Ph groups were used. 4,4 -(Diethylsilylene)bis(phenyl chloroformate), 4,4 -(ethylmethylsilylene)bis(phenyl chloroformate) and 4,4 -(diethylgermylene)bis(phenyl chloroformate) were obtained as a slightly yellow oil, while 4,4 -(diphenylsilylene)bis(phenyl chloroformate), 4,4 -(methylphenylsilylene)bis(phenyl chloroformate) and 4,4 -(diphenylgermylene)bis(phenyl chloroformate) were obtained as a white solid. The new bi-functional monomers were characterized by FT-IR, 29 Si-, 13 C-and 1 H-NMR spectroscopy and elemental analysis. The T m of the products in general was higher in samples containing germanium as the central atom, compared to those containing silicon.

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“…The basic synthetic route for these derivatives was first reported by Davidsohn et al [3] and since it has been used for preparing several bisphenols (Fig. 3).…”

Section: Synthesis Of Bisphenols: Bis(4-hydroxyphenyl)r 1 R 2 -Silanementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and characterization of new bi-functional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates)

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Concha

et al. 2007

Designed Monomers and Polymers

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“…Thus, it is possible to find structures based on bis(p-hydroxyphenylene) [7][8][9][10][11][12][13] , bis(pbromophenylene) 14 , bis(aminophenylene)meta and para isomers, 10,14-16 and bis(p-carboxyphenylene) 11,17,18 , bis(p-ch orocarbonylphenylene) 11,[17][18][19][20][21] , bis(pcarboxyalkylphenylene) 20,22 , bis(p-(3,4 dicarboxyphenylene)) dianhydride 16,[23][24][25][26] , bis(p-isocyanatephenylene) 27 , bis(p-carbohydrazidophenylene) 22 , bis(p acidazidephenylene) 14 and bis(p-chloroformatephenylene) 13,28 moieties. The several polymers obtained from these aromatic monomers show low chain-mobility with low to moderate glass transition temperatures (Tg).…”

Section: Introductionmentioning

confidence: 99%

DIFUNCTIONAL SILARYLENE-CONTAINING ALIPHATIC COMPOUNDS: SYNTHESIS AND CHARACTERIZATION OF BIS(p (CARBOXYMETHYL)PHENYL)(R)PHENYLSILANE AND BIS(p-(2-AMINOETHYL)PHENYL)(R)PHENYLSILANE (R = Me, Ph)

Terraza

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Lembach

2010

J. Chil. Chem. Soc.

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This work describes the synthesis of aliphatic diacids and diamines containing a silarylene moiety in the structure. These compounds can be employed as monomers for the synthesis of poly(amides) and poly(esters) or other condensation polymers. Thus, bis(p-methylphenylen)(R)phenylsilanes were obtained from p-bromotoluene and dicloro(R)phenylsilane (R= Me, Ph). Also, the dibenzyl nitrile compounds bis(p-(cyanomethyl)phenylen)(R)phenylsilanes were synthesized from the respective bis(p-(bromomethyl)phenylen) (R)phenylsilanes derivatives. The hydrolysis of the dibenzyl nitrile derivatives gives the respective diacids bis(p-(carboxymethyl)phenylen)(R)phenylsilanes with low yield. A direct Grignard reaction type was also studied using as precursors the dibenzyl bromide compounds. In a second stage, the synthesis of the phenethylamine bis(p-(2-aminoethyl)phenylen)(R)phenylsilane was studied by the reduction of the dibenzyl nitrile compounds. All compounds were characterized by IR-TF, 1 H, 13 C and 29 Si NMR.

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The preparation of organolithium reagents and intermediates

Leroux¹,

Schlosser

Zohar

et al. 2004

The Chemistry of Organolithium Compounds

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Organometallic bis(p-hydroxyphenyl) derivatives of group IV elements and related compounds

Cited by 45 publications

References 14 publications

Synthesis and characterization of new bi-functional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates)

Synthesis and characterization of new bi-functional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene)bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates)

DIFUNCTIONAL SILARYLENE-CONTAINING ALIPHATIC COMPOUNDS: SYNTHESIS AND CHARACTERIZATION OF BIS(p (CARBOXYMETHYL)PHENYL)(R)PHENYLSILANE AND BIS(p-(2-AMINOETHYL)PHENYL)(R)PHENYLSILANE (R = Me, Ph)

The preparation of organolithium reagents and intermediates

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