2007
DOI: 10.1016/j.jorganchem.2006.10.069
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The difference in reactivity of (−)-mono and dimenthyl vs. diethyl alkylphosphonates in the α-lithiation reaction: Carbanionic synthesis of unknown (−)-dimenthyl 1-iodoalkylphosphonates and their first use in the radical iodine atom transfer addition (I-ATRA) and cyclisation (I-ATRC) reactions

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Cited by 9 publications
(6 citation statements)
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“…According to the method mentioned above, we have obtained both enantiomeric (–)‐ and (+)‐dimenthyl phosphites 1a and 1b (Fig. ) for which the spectral data and the value of [α] D were consistent with the literature . The enantiomeric sulfinimines (Fig.…”
Section: Resultssupporting
confidence: 80%
See 1 more Smart Citation
“…According to the method mentioned above, we have obtained both enantiomeric (–)‐ and (+)‐dimenthyl phosphites 1a and 1b (Fig. ) for which the spectral data and the value of [α] D were consistent with the literature . The enantiomeric sulfinimines (Fig.…”
Section: Resultssupporting
confidence: 80%
“…The starting (–)‐dimenthyl phosphite 1a was obtained for the first time by Miłobędzki in 1931 in the reaction of (–)‐menthol and phosphorus trichloride and subsequent hydrolysis of dimenthyl chlorophosphite formed. Later on, this procedure was successfully repeated by Kafarski and Bałczewski , who reported its spectral data as well as elemental analysis and optical rotation value. According to the method mentioned above, we have obtained both enantiomeric (–)‐ and (+)‐dimenthyl phosphites 1a and 1b (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…There are other peaks in the spectra at 31 ppm interval due to spinning sidebands, and also smaller peaks at 30–35 ppm which is most likely due to small amounts of diethyl phosphite in the material. This is because their chemical shift closely matches with that of similar compounds such as methyl phosphonic acid diethyl ester (34.8 ppm) and the coupling constant of 680 Hz corresponds to PH coupling that exists in diethyl phosphite,50, 51 but not in phosphonated SEBS.…”
Section: Resultsmentioning
confidence: 70%
“…Dimenthyl H‐Phosphonate: 26 After kugelrohr distillation, 4.39 g (49 %) of a clear liquid was obtained. 1 H NMR (400 MHz, CDCl 3 ): δ = 6.91 (d, 1 J HP = 686.8 Hz, 1 H), 4.28–4.18 (m, 2 H), 2.20–2.16 (m, 2 H), 2.15–2.04 (2 m, 2 H), 1.69, 1.65 (2 br.…”
Section: Methodsmentioning
confidence: 99%