Zur Kenntnis der Sulfos�ureester

Drahowzal, F.; Klamann, Dieter

doi:10.1007/bf00900841

Cited by 25 publications

(8 citation statements)

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“…of water, 464.9 grams (1.40 moles) of 0'-hepty 1 alcohol and 290.0 grams (0.68 mole) of 1,6-hexanediol bis(p-toluenesuIfonate) (36, 88) \ melting point 71°to 72°C. (10). Distillation gives 200 grams (.39% yield) of (boiling point 142°to 145°C.…”

mentioning

confidence: 99%

Partially Fluorinated Esters and Ethers as Temperature-Stable Liquids

Faurote¹,

Henderson²,

Murphy³

et al. 1956

Ind. Eng. Chem.

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confidence: 99%

Partially Fluorinated Esters and Ethers as Temperature-Stable Liquids

Faurote¹,

Henderson²,

Murphy³

et al. 1956

Ind. Eng. Chem.

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“…The organic layer was dried over Na 2 SO 4 and concentrated under vacuum and the crude product purified by silica gel chromatography (CH 2 Cl 2 ). Azeotrope distillation with benzene (tosylates 21 , 35 , and 38 were dried in a vacuum desiccator over P 2 O 5 ) yielded 18.0 g (96%) of 4-methylbenzenesulfonic acid, propyl ester ( 10 ) as a clear oil: bp 153 °C (lit . 154−156°); 1 H NMR δ 0.90 (t, 3H, J = 7.3 Hz), 1.62−1.73 (m, 2H), 2.45 (s, 3H), 3.99 (t, 2H, J = 7.2 Hz), 7.36 (d, 2H, J = 8.3 Hz), 7.90 (d, 2H, J = 8.3 Hz).…”

Section: Methodsmentioning

confidence: 99%

“…4-Methylbenzenesulfonic Acid, Isopropyl Ester (32). Prepared as a clear oil in 94% yield: bp 129 °C (dec) (lit …”

Section: Methodsmentioning

confidence: 99%

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Scope and Utility of a New Soluble Copper Catalyst [CuBr−LiSPh−LiBr−THF]: A Comparison with Other Copper Catalysts in Their Ability to Couple One Equivalent of a Grignard Reagent with an Alkyl Sulfonate

et al. 1997

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A mixture of equal amounts of CuBr−SMe2, LiBr, and LiSPh in THF at 0 °C furnished a new soluble copper catalyst that was highly efficient at coupling primary, secondary, tertiary, aryl, vinyl, and allylic Grignard reagents to primary tosylates and primary Grignard reagents to secondary tosylates and mesylates, all with the use of only 1 equiv of Grignard reagent. The new catalyst was shown to be much more reactive than copper catalysts CuBr and Li2CuCl4 and more efficient in the transference of secondary and tertiary alkyl groups than lower order cuprates (Gilman reagents) and demonstrated more reactivity than the lower order cuprates with its ability to couple primary Grignard reagents to secondary sulfonates. The Grignard reagent/catalyst system was compatible with an ester functionalized tosylate, thus proving to be more chemoselective than a Grignard reagent without the catalyst. The catalyst exhibited good reactivity below room temperature, and with the addition of 6% v/v of HMPA to the catalyst solution, excellent yields of coupled product were obtained within a 25−67 °C temperature range. 1H NMR demonstrated that the catalyst solution consisted of several species that most likely were composed of copper ligated with thiophenol, THF, and LiBr in aggregated forms.

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“…Phenylmagnesium bromide 1a was prepared in THF by standard method and its concentration was found by titration prior to use [41]. Phenyl arenesulfonates 2a-e were prepared by the published procedures using arenesulfonyl chlorides and phenol and were confirmed by melting points, IR and 1 H NMR spectroscopy [25,33,[42][43][44] Kinetic procedure for the reaction of phenylmagnesium bromide 1a with phenyl arenesulfonates 2a-e: The kinetics were followed by measuring concentration of remaining phenyl arenesulfonate by GC analysis. Phenyl arenesulfonate, toluene and internal standard were thermostated at 90°C in a jacketed two necked reaction vessel of approximately 25 ml capacity equipped with a reflux condenser and a magnetic stirrer.…”

Section: Reagentsmentioning

confidence: 99%