Using hydrogen bonding to control carbamate C-N rotamer equilibria

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7258-7262

  Moraczewski, Alexei L ^a   Banaszynski, Laura A ^a   From, Aaron M ^a   White, Courtney E ^a   Smith, Bradley D ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000459942     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980644d     Document Type: Article

References (19)

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11. s/a = 0.05 for 3a and 4a at -20°C were determined by integrating the tert-butyl resonances for the anti rotamer at 1.49 ppm and the syn rotamer at 1.55 ppm. The syn NH signal was too weak to be observed; however, Nudelman and coworkers found that in the absence of hydrogen bonding the syn NH and anti NH chemical shifts differ by less than 0.1 ppm.6 Therefore, a reasonable estimate of the syn NH chemical shift for 3a in the absence of 1 is 8.64 ppm at -20 °C in CDC13.
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