Living ring-opening polymerization of N-sulfonylaziridines: Synthesis of high molecular weight linear polyamines

Journal of the American Chemical Society

Volumn 127, Issue 50, 2005, Pages 17616-17617

  Stewart, Ian C ^a   Lee, Cameron C ^a   Bergman, Robert G ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; N SULFONYLAZIRIDINE DERIVATIVE; POLYAMINE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; DISPERSION; ENANTIOMER; HYDRODYNAMICS; POLYMERIZATION; REACTION ANALYSIS; RING OPENING; SOLUBILITY;

EID: 29344440041     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0554357     Document Type: Article

References (24)

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13. Other activating groups were tested (e.g., diphenylphosphinyl, acetyl, ethylcarbanioyl), but only sullonylaziridines were found to afford the desired molecular weights and low polydispersities.
14. See Supporting Information.
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16. Unfortunately, the polymerization of N-p-toluenesulfonylaziridine afforded insoluble low molecular weight oiigomers under a variety of reaction conditions. Due to the insolubility of the product in all solvents tested, we have not further pursued this reactivity. There are two patents detailing similar results for the polymerization of this monomer: (a) Berchet, G. J. U.S. Patent 2.269.997, 1942.
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19. End group analysis of MALDI-TOF MS spectra did suggest incorporation of the amide nucleophile into the polymer chain.
20. 1H TOCSY NMR: see Supporting Information.
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