1986
DOI: 10.1021/ma00157a001
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Synthesis and ring-opening polymerization of bicyclic lactones containing a tetrahydropyran ring. 2,6-Dioxabicyclo[2.2.2]octan-3-one

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Cited by 20 publications
(10 citation statements)
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“…In accordance with the poor cationic polymerizability, 3 was not hydrolyzed to a detectable extent, whereas 1, 6,8-dioxabicyclo-[3.2.1]octan-7-one (8), and e-caprolactone as a reference compound were hydrolyzed under the identical conditions to give first-order rate constants of 5.6 X 10"5, 1.6 X 10"5, and 0.4 X 10"5 s"\ respectively. These data are in conformity with the high reactivity in cationic polymerization of 1 The bicyclic lactone 3 was polymerized with anionic and coordination initiators such as butyllithium, lithium benzophenone ketyl, and tetraisopropyl ti tanate. However, the yields and number-average molecular weights of the polymers were quite low.…”
Section: Resultssupporting
confidence: 80%
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“…In accordance with the poor cationic polymerizability, 3 was not hydrolyzed to a detectable extent, whereas 1, 6,8-dioxabicyclo-[3.2.1]octan-7-one (8), and e-caprolactone as a reference compound were hydrolyzed under the identical conditions to give first-order rate constants of 5.6 X 10"5, 1.6 X 10"5, and 0.4 X 10"5 s"\ respectively. These data are in conformity with the high reactivity in cationic polymerization of 1 The bicyclic lactone 3 was polymerized with anionic and coordination initiators such as butyllithium, lithium benzophenone ketyl, and tetraisopropyl ti tanate. However, the yields and number-average molecular weights of the polymers were quite low.…”
Section: Resultssupporting
confidence: 80%
“…The solution was filtered and the solvent was removed by rotary evaporation. The oily residue was distilled under reduced pressure: yield 135.2 g (87%); bp 75-80 °C (8 mmHg); IR (neat) 3060 (y-c-h), 1760 (^c-o)> 1650 (roc), 1200 (vc-o-cX 1080 (rc-o-c) cm NMR (CDC13) 6.42 (d, J = 6.2 Hz, 1 , H-6), 4.76 (m, 1 H, H-5), 4.45 (m, 1 , H-2), 4.24 (q, J = 7.2 Hz, 2 H, Ctf2CH3), 1.9-2.2 (m, 4 , 2H-3 and 2H-4), 1.30 (t, J = 7.2 Hz, 3 H, CH2CH3); 13C NMR (CDClg) 170.96 (C=0), 142.63 (C-6), 100.70 (C-5), 73.12 (C-2), 61.06 (CH2CH3), 24.88 (C-3), 18.52 (C-4), 14.18 (CH2CH3).…”
Section: Methodsmentioning
confidence: 99%
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“…10 potassium hydroxide. Transesterification took place during the saponification, and subsequent neutralization of the reaction products with hydrochloric acid gave the monoesters 12-14, respectively.…”
Section: Monomer Synthesismentioning
confidence: 99%
“…(5) Worsfold, D. J.; Bywater, S. Macromolecules 1978, 11, 582. (6) Glaze, W. H.; Hanicak, J. E.; Moore M. L.; Chaudhuri, J. J. Organometal. Chem.…”
Section: References and Notesmentioning
confidence: 99%