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Volumn 62, Issue 12, 1997, Pages 3858-3861

Spontaneous Lossen Rearrangement of (Phosphonoformyl)hydroxamates. The Migratory Aptitude of the Phosphonyl Group

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EID: 0013260748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962075k     Document Type: Article
Times cited : (29)

References (54)
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    • note
    • 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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    • Instruments and general techniques are described in refs 25 and 29
    • Instruments and general techniques are described in refs 25 and 29.


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