Mode of nucleophilic addition to epichlorohydrin and related species: chiral aryloxymethyloxiranes

Mcclure, D. E.; Arison, Byron H.; Baldwin, John J.

doi:10.1021/ja00507a047

Cited by 114 publications

(55 citation statements)

References 4 publications

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“…18 The dioxirane compound 3 having a biphenyl moiety has also been synthesized by a similar route from racemic epichlorohydrin and 4,4Ј-dihydroxybiphenyl.…”

Section: Synthesis Of Oxiranesmentioning

confidence: 99%

“…RAC1 was prepared by the procedure developed by McClure et al 18 for aryloxymethyloxiranes. Into a 250-ml three-necked flask fitted with a reflux condenser and magnetic stirrer were introduced 3.44 g (0.0172 mol) of 4-methoxy-4Ј-hydroxybiphenyl in 100 ml of anhydrous acetone, 2.62 g (0.019 mol) of K 2 CO 3 , and 2.4 ml of distilled (R,S)-epichlorohydrin.…”

Section: Experimental Procedures Synthesis Of Oxiranes (Rs)-[(4-methmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Taton

Borgne²,

Chen³

et al. 1998

Chirality

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“…18 The dioxirane compound 3 having a biphenyl moiety has also been synthesized by a similar route from racemic epichlorohydrin and 4,4Ј-dihydroxybiphenyl.…”

Section: Synthesis Of Oxiranesmentioning

confidence: 99%

Section: Experimental Procedures Synthesis Of Oxiranes (Rs)-[(4-methmentioning

confidence: 99%

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Taton

Borgne²,

Chen³

et al. 1998

Chirality

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“…21 Lactones 17b-d,23 17f-g,23 and 18a-p4.25 have been obtained using the general method of preparation given in the respective references. The spectroscopic data were in accordance with the expected structures.…”

Section: Racemates and Enantiomersmentioning

confidence: 99%

“…However, the conservation of the configuration during the reaction step involving the nucleophilic substitution with phenol is strongly dependent on the reaction conditions, on the leaving group Y on the oxirane and on the substituent X on the phenolic moiety. 21 The direct preparation of the enantiomers of arylglycidylethers by chromatographic resolution on CTA I bypasses this problem and provides an easy access to these useful chiral synthons in optically pure form. Various arylglycidylether derivatives obtained by reaction of epichlorohydrin with phenol or naphthol derivatives have been chromatographed on CTA I (Fig.…”

Section: Aandglpcidglethermentioning

confidence: 99%

Preparation of chiral building blocks and auxiliaries by chromatography on cellulose triacetate (CTA I): Indications for the presence of multiple interaction sites in CTA I

Francotte

Wolf

1990

Chirality

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Due to the increasing demand for optically active compounds, the development of methods supplying optically pure isomers is intensively progressing. Among these methods the chromatographic resolution on chiral stationary phases is very promising, although only a limited number of preparative applications have been reported so far. In this work, we demonstrate that especially cellulose triacetate I (CTA I) as a chiral phase presents a number of advantages for this purpose. The broad applicability and the high loading capacity of CTA I are particularly important features for preparative chromatography. Nevertheless, slight structural modifications of the racemates to be resolved can often strongly improve the resolution. This strategy has been applied to numerous practical problems and is illustrated in this work taking as examples some chiral building blocks and auxiliaries. Moreover, a systematic investigation of the influence of a substituent in the para-position of the phenyl ring for different series of aromatic compounds led to the conclusion that a large number of different interaction sites must be present in the chiral environment of CTA I.

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“…Other bis(epoxide)s, such as 4,4Ј-diglycidyloxyphenyl ether (2d), 6,6Ј-digycidyloxy-4,4,4Ј,4Ј,7,7Ј-hexamethyl bis-2,2Ј-spirochroman (2e), bisphenol S diglycidyl ether (2f) and 4,4Ј-diglycidyloxyphenone (2g), were synthesized from epichlorohydrin with corresponding bis(phenol)s; 4,4Ј-dihydroxyphenyl ether, 6,6Ј-dihydroxy-4,4,4Ј,4Ј,7,7Ј-hexamethyl bis-2,2Ј-spirochroman, bisphenol S and 4,4Ј-dihydroxyphenone in 94, 44, 79 and 23% yields, respectively, according to the reported methods. 20 Tetrabutylammonium bromide (TBAB) was recrystallized from dry ethyl acetate. tetrabutylammonium chloride (TBAC), tetrabutylammonium iodide (TBAI), tetraethylammonium bromide (TEAB), tetrabutylphosphonium chloride (TBPC), tetrabutylphosphonium bromide (TBPB), tetraphenylphosphonium chloride (TPPC), and tetrabutylphosphonium bromide (TPPB) were used as received.…”

Section: Experimental Materialsmentioning

confidence: 99%

Novel synthesis of polyethers by the polyaddition of bis(epoxide)s with bis(phosphinate)s

Chen

Kameyama

Nishikubo

1999

J. Polym. Sci. A Polym. Chem.

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Mode of nucleophilic addition to epichlorohydrin and related species: chiral aryloxymethyloxiranes

Cited by 114 publications

References 4 publications

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Preparation of chiral building blocks and auxiliaries by chromatography on cellulose triacetate (CTA I): Indications for the presence of multiple interaction sites in CTA I

Novel synthesis of polyethers by the polyaddition of bis(epoxide)s with bis(phosphinate)s

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