Formation, structure and conformational dynamics of highly substituted diphenylcarbonates

Chemistry - A European Journal

Volumn 6, Issue 19, 2000, Pages 3522-3530

  Godt, Adelheid ^a   Ünsal, Ömer ^a   Enkelmann, Volker ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Carbonates; Conformation analysis; Conformation dynamics; Template synthesis

Indexed keywords

4 HYDROXYBENZOIC ACID; BENZOIC ACID; BIPHENYL DERIVATIVE; CARBONIC ACID DERIVATIVE;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 0034596919     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001002)6:19<3522::AID-CHEM3522>3.0.CO;2-R     Document Type: Article

References (24)

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13. On working with the combination sodium phenolate/diphosgene, we found the following: if diphosgene is added first to a suspension of sodium hydride in THF followed by ethyl 4-hydroxybenzoate, no gas evolution was observed when the phenol was added. Aqueous work-up gave mainly the starting material ethyl 4-hydroxybenzoate. On the other hand, if the phenol was added first to the suspension of sodium hydride (1.5 equiv), the expected gas evolution was observed. Addition of diphosgene followed by aqueous work-up gave the crude product containing mainly (97%) carbonate, although the excess of NaH had not been removed prior to the addition of diphosgene. Furthermore, the preparation of chloroformates with phosgene by the addition of a phenol to the suspension of phosgene/NaH/THF failed. Gas evolution was not observed. If someone has an explanation for this observation, we would highly appreciate it if he would share it with us.
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15. 2 or several F) with pyridine or DMAP has been reported: D. J. Brunelle, Tetrahedron Lett. 1982, 23, 1739; H. Han, K. D. Janda, J. Am. Chem. Soc. 1996, 118, 2539.
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19. We use the words "cis" and "trans" according to their use in the carbonate literature (e.g. ref. [16]), that is not obeying the Cahn-Ingold-Prelog rules.
20. The carbonates 7b and 8b were used for the dynamic measurements instead of the carbonates 7c and 8c because of better solubility and especially because of the larger differences in the chemical shift of the aromatic signals. The structures of 7b and 8b in the crystal are expected to be very similar to those found for 7c and 8c. Preliminary data for 7b indicate that this assumption is correct. However, the quality of the crystals was not sufficient owing to a disorder of some of the ethoxyphenyl moieties.
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24. 2 (676.416): C 65.70, H 3.58; found: C 65.66, H 3.60.