Use of the N–O Bonds in N -Mesyloxyamides and N -Mesyloxyimides To Gain Access to 5-Alkoxy-3,4-dialkyloxazol-2-ones and 3-Hetero-Substituted Succinimides: A Combined Experimental and Theoretical Study.

In the reactions with NaN SB 3 sb , NaOAc, NaCl and H SB 2 sb O, the formation of the respective substitution products was detected by SP 1 sp H NMR spectroscopy and mass spectrometry of the reaction solution. SP 1 sp H NMR (400 MHz, CDCl SB 3 sb ): = 7.39-7.31 (m, 3 H, Ar- I H i ), 7.22-7.20 (m, 2 H, Ar- I H i ), 4.04-4.00 (m, 1 H, PhC I H i CO), 3.21 (dd, I J i = 18.6, 9.3 Hz, 1 H, C I H i HCO), 2.81 (dd, I J i = 18.6, 3.6 Hz, 1 H, CH I H i CO). SP 1 sp H NMR (400 MHz, DMSO- I d i SB 6 sb ): = 11.47 (bs, 1 H, N I H i ), 7.51-7.29 (m, 5 H, Ar- I H i ), 3.06 (d, I J i = 18.0 Hz, 1 H, C I H i HCO), 2.94 (d, I J i = 18.0 Hz, 1 H, CH I H i CO). SP 1 sp H NMR (400 MHz, CDCl SB 3 sb ): = 8.48 (bs, 1 H, N I H i ), 7.43-7.37 (m, 5 H, Ar- I H i ), 3.23 (d, I J i = 18.4 Hz, 1 H, C I H i HCO), 3.10 (d, I J i = 18.4 Hz, 1 H, CH I H i CO). [Extracted from the article]