THERMAL DEGRADATION OF DIMERS OF PHOSPHOLES

References

• 1983 . Taken from the doctoral dissertation of K.C.C. Duke University .
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• Quin , L. D. , Caster , K. C. , Kisalus , J. C. and Mesch , K. A. 1984 . J. Am. Chem. Soc. , 106 : 7021
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• Caster , K. C. and Quin , L. D. 1983 . Tetrahedron Lett. , 24 : 5831
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• The use of FT NMR for 31P does not necessarily provide a quantitative analysis of a complex mixture unless long pulse delays are used to accommodate species with long relaxation times. Nevertheless, an approximate analysis showing trends was considered satisfactory for the present work
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• Quin , L. D. , Lloyd , J. R. and Caster , K. C. 1983 . J. Chem. Soc. Chem. Commun. , : 1302
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• Quin , L. D. and Rao , N. S. 1983 . J. Org. Chem. , 48 : 3754
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• A referee suggested that decomposition of 3-methyl-1-phenylphosphole after formation could account for its low concentration in the product mixture. A solution (0.08 M) in xylene was heated at 126°C for 17 hr: about 40% remained unchanged. The only other 31P NMR signal (unassigned) appeared at δ -9.3. The complexity of the spectrum for the thermolysis product of dimer 14 hindered the detection of such a species in the mixture, but even if present, the combined concentration of this species and the remaining phosphole would still not indicate that a significant amount of phosphole had formed in the original thermolysis
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• Quin , L. D. 1981 . “ chapter 6 ” . In The Heterocyclic Chemistry of Phosphorus , New York : Wiley-Interscience . Discussed in
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• Melting points were taken on a Mel-Temp apparatus and are corrected; boiling points are uncorrected. Proton NMR spectra were obtained on a JEOL MH-100 or an IBM NR-80 spectrometer at 100 MHz and 80 MHz, respectively, using tetramethylsilane (TMS) as an internal standard, unless otherwise noted. Carbon-13 NMR spectra were obtained on a JEOL FX-90Q (including the INEPT program) or a JEOL FX-60 spectrometer at 22.5 MHz and 15.0 MHz, respectively, using TMS as an internal standard, unless otherwise noted. Phosphorus-31 NMR spectra were obtained on a JEOL FX-90Q or a Bruker HFX-10 spectrometer at 36.2 MHz and 36.4 MHz, respectively, using 85% H3PO4 as an external standard with an internal deuterium lock; positive chemical shifts (ppm) are downfield of the reference. Broad-band proton noise-decoupling was employed on all carbon-13 and phosphorus-31 NMR spectra. Mass spectra were obtained on a Hewlett Packard 5992A GC-MS at 70 eV or on an AEI MS 903 Spectrometer. Elemental analyses were performed by MHW Laboratories, Phoenix, AZ. Procedures involving trivalent phosphorus compounds were performed under a nitrogen or an argon atmosphere
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