Probing the reactivity of solid supports via Hammett relationships

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6357-6363

  Gerritz, Samuel W ^a   Trump, Ryan P ^a,b   Zuercher, William J ^a  

^a GLAXOSMITHKLINE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; ANILINE DERIVATIVE; ESTER; MACROGOL; POLYSTYRENE; SOLVENT;

ARTICLE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; TECHNIQUE;

EID: 0034641327     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9943187     Document Type: Article

References (44)

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36. In all cases, yields exceeded 85% (based on initial polymer loading).
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38. The solution-phase and PS lantern competition experiments were carried out only once, while the MA/DMA crown and LLPS crown competition experiments were carried out in triplicate.
39. It is worth noting that the solution-phase competition experiments could be carried out in the same flask as the solid-phase experiments, but technical considerations (i.e., isolating the desired amide products from over 100 equiv of each substituted aniline) prompted us to conduct the solution-phase experiments separately.
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43. 1H NMR studies of solid supports: (a) Kiefer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Selfer, A. M.; Gerritz, S. W. J. Comb. Chem. 2000, 2, 127.
44. Bing Yan's contribution to ref 2b (pp 447 and 448) also highlights the complex relationship between solid support and solvent.