1964
DOI: 10.1016/s0040-4039(00)70409-6
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Phosphororganische verbindungen XLIII untersuchungen zum sterischen verlauf der PO-aktivierten Olefinierung

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Cited by 19 publications
(10 citation statements)
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“…In an earlier paper we described the results of an investigation into the preparation of stilbene from the diastereoisomeric 1,2diphenyl-2-diphenylphosphinoylethan-1-01s (1) and (2) in order to clarify some details of the work by Horner and Klink on this system. As expected for a syn elimination mechanism, treatment of the threo-isomer (2) with base gave (E)-stilbene stereospecifically. However under most conditions, base treatment of the erythro-isomer (1) also gave predominantly (E)stilbene, together with variable amounts of benzyldiphenylphosphine oxide.…”
supporting
confidence: 67%
See 1 more Smart Citation
“…In an earlier paper we described the results of an investigation into the preparation of stilbene from the diastereoisomeric 1,2diphenyl-2-diphenylphosphinoylethan-1-01s (1) and (2) in order to clarify some details of the work by Horner and Klink on this system. As expected for a syn elimination mechanism, treatment of the threo-isomer (2) with base gave (E)-stilbene stereospecifically. However under most conditions, base treatment of the erythro-isomer (1) also gave predominantly (E)stilbene, together with variable amounts of benzyldiphenylphosphine oxide.…”
supporting
confidence: 67%
“…In our previous work,' treatment of the erythro-isomer (1) with sodium hydride in DMSO at 25 "C gave (E)-stilbene (78%) and benzyldiphenylphosphine oxide (19%). Treatment of the erythro-dibenzophosphole oxide (6) under the same conditions gave a mixture of stilbenes (91%) comprising (2)stilbene (89%) and (E)-stilbene (1 1%). Clearly the desired enhancement of the syn-elimination pathway from (6) had occurred.…”
Section: Ohmentioning
confidence: 99%
“…However, when R' is p'-branched, the stereoselectivity swings dramatically towards the anti diastereomer. These compounds are reduced by NaBH,/CeCI, to give anti p-hydroxy phosphane oxides anti-2, often with no trace of the syn isomers (entries [4][5][6][7][8][9][10][11][12][13][14].…”
Section: Luche Reduction Of P-0x0 Phosphane Oxidesmentioning
confidence: 99%
“…The Wittig-Horner reaction employs metallated organophosphine oxides, with the original preparations involving metallation of benzyldiphenylphosphine oxide by potassium-tert-butoxide [2]. When lithium bases are used, the reaction yields an intermediate adduct in which the lithium counter ion binds strongly to the oxyanion formed in the process, preventing attack on the diphenylphosphoryl group [3]. Following acidification, b-hydroxyphosphine oxides are obtained, and these are stable and usually crystalline compounds at room temperature [3,4] ( Fig.…”
Section: Introductionmentioning
confidence: 99%
“…0.23 g (2.00 mmol) of BzNa and 0.43 g (2.00 mmol) of Ph 2 P(O)CH3 were reacted together in a mixture of 7 mL of thf, 3.5 mL of hexane, and 0.41 mL (2.00 mmol) of 15-crown-5. Briefly heating to reflux followed by filtration afforded a brown solution.…”
mentioning
confidence: 99%