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In the N-alkylthiocarbamoylphosphonates studied by Tashma and Masson (ref 13), syn or Z mean that the phosphorus and the NH which are the groups of lower priority (P is lower than S and H is lower than C) are situated on the same side of the amide C-N bond. In oxygen-containing carbamoylphosphonates the same configuration will be called E, since the replacement of S by O changes the order of priorities (P is higher than O). In N-methyl(phosphonoformyl)hydroxamic acid, 2c, the order of priorities changes again due to the replacement of the N-H by N-OH (O is higher than C) and in the Z-isomer the P and the N-methyl groups are anti across the C-N bond (Scheme 4). Consequently, for clarity in the present discussion, we will refer to the situation of N-methyl or N-alkyl groups as syn or anti relative to the phosphorus regardless of whether these are of C=O or C-S, or N-H or N-OH amides.
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3Jpc values of 17-25 Hz for E and 4-11 Hz for Z isomers) than those we found for (E)- and (Z)-2c, still the trend is consistent. Examination of the spectral data presented by Masson (ref 13), however, reveals VPC values similar to those found by us. This paper reports VPC values of 8.1-8.7 Hz for N-alkyl carbons anti relative to phosphorus across a thioamide C-N bond.
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3Jpc values of 17-25 Hz for E and 4-11 Hz for Z isomers) than those we found for (E)- and (Z)-2c, still the trend is consistent. Examination of the spectral data presented by Masson (ref 13), however, reveals VPC values similar to those found by us. This paper reports VPC values of 8.1-8.7 Hz for N-alkyl carbons anti relative to phosphorus across a thioamide C-N bond.
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3Jpc values of 17-25 Hz for E and 4-11 Hz for Z isomers) than those we found for (E)- and (Z)-2c, still the trend is consistent. Examination of the spectral data presented by Masson (ref 13), however, reveals VPC values similar to those found by us. This paper reports VPC values of 8.1-8.7 Hz for N-alkyl carbons anti relative to phosphorus across a thioamide C-N bond.
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