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Oxygen-17 NMR spectroscopy (natural abundance) of heterocycles: anhydrides

Oxygen-17 NMR spectroscopy (natural abundance) of heterocycles: anhydrides. Vasquez, P. C.; Boykin, D. W.; Baumstark, A. L. (Dep. Chem.Some commonly used reagents like 4160-82-1 is used in this experiment., Georgia State Univ., Atlanta, GA 30303-3083, USA). Magn. Reson. Chem., 24(5), 409-14 (English) 1986. CODEN: MRCHEG. ISSN: 0749-1581. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) 17O NMR spectra were recorded for several series of anhydrides (￡0.5M) in dried MeCN at 75°. The 17O NMR data for simple anhydrides were highly sensitive [acetic anhydride, d 411 ppm (C:O), d 273; glutaric anhydride (I), d 396 ppm (C:O), d 288 ppm; succinic anhydride d 376 (C:O), d 301; maleic anhydride, d 401 (C:O), d 252; phthalic anhydride (II), d 374 (C:O), d 263]. The 17O NMR data were sensitive to ring size and conformation. Substituent effects on a series of maleic anhydrides could be rationalized in terms of electronic effects. In contrast, the 17O NMR data for polycyclic succinic anhydrides showed that the chem. shifts of the carbonyl oxygens were roughly const., while those of the central oxygens were sensitive to structure. The 17O NMR data for homophthalic anhydride [d 397 (C:O), d 372 (C:O), d 273] were consistent with those for I and II; the data for pyridine-2,3-dicarboxylic anhydride [d 383 (C:O), d 380 (C:O), d 263] could be rationalized in terms of electronic effects, and those for 3,4-dihydronaphthalene-1,2-dicarboxylic anhydride [d 392 (C:O), d 387 (C:O), d 252] were explained by compressional and electronic effects. .