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Original Articles

CYCLIC ORGANOPHOSPHORUS COMPOUNDS. PART XVI1. MASS SPECTROMETRIC FRAGMENTATION OF SOME 5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN 2-OXIDES AND 2-SULPHIDES

Pages 307-314 | Received 03 Mar 1980, Accepted 06 May 1980, Published online: 19 Dec 2006

References

  • Edmundson , R. S. and Forth , C. I. 1980 . Phosphorus-Sulfur , 8 : 315 Part XV
  • Francis , G. W. , Tjessem , K. , Dale , A. and Gramstad , T. 1976 . Acta Chem. Scand. , B30 : 31
  • Murai , A. and Kainosho , M. 1976 . Organic Mass Spectrometry , 11 : 175
  • Jakobsen , P. , Treppendahl , S. and Wieczorkowski , J. 1972 . Organic Mass Spectrometry , 6 : 1303
  • Edmundson , R. S. 1964 . Tetrahedron , 20 : 2781 Tetrahedron, 21, 2375 (1965); J. Chem. Soc., C, 1635 (1967)
  • Bartle , K. D. , Edmundson , R. S. and Jones , D. W. 1967 . Tetrahedron , 23 : 1701
  • Edmundson , R. S. and Mitchell , E. W. 1968 . J. Chem. Soc., C , : 3033
  • Edmundson , R. S. and Moran , T. A. 1971 . J. Chem. Soc., C , : 3437
  • Modro , T. A. , Lawry , M. A. and Murphy , E. W. 1978 . J. Org. Chem. , 43 : 5000 This compound has since been described by, as having m.p. 159–160°C
  • Nikoletić , M. , Borcic , S. and Sunko , D. E. 1967 . Tetrahedron , 23 : 649
  • The corresponding t-butoxy compound decomposes thermally at ca. 85°C. Its mass spectrum exhibits strong M-15 ions but otherwise, as might be expected, its spectrum is very similar to that of the cyclic acid
  • Desmarchelier , J. M. , Wustner , D. A. and Fukuto , T. R. 1976 . Residue Reviews , 63 : 77 Springer-Verlag
  • Safe , S. and Hutzinger , O. 1973 . “ Chap. 21 ” . In Mass Spectrometry of Pesticides and Pollutants , 189 Cleveland, Ohio : C.R.C. Press .
  • Zielinske , B. and Stec , W. J. 1978 . (Org. Mass Spectrometry , 13 : 65 A. study by of the fragmentation behaviour of diastereoisomeric 4 - methyl - 2 - amino - 1,3,2 - dioxaphosphorinan 2-sulphides showed that the cis and trans isomers of each of the 2-d 5-anilino-4-methyl-,2-NN-dimethylamino-4-methyl-, and 2-NN-dimethylamino-4-d 3-methyl- compounds, as well as trans-2-NN-dimethylamino-4-methyl-4,6,6-d 3-1,3,2-dioxaphosphorinan 2-sulphide, lose sulphur exclusively as HS, whereas the cis isomer of the last compound loses sulphur as both HS and DS in approximately equal amounts. The lack of participation of an amide hydrogen atom in the release of SH was confirmed for the 4-methyl-1,3,2-dioxaphosphorinan 2-sulphide series. D. Boucho and J. Dreux (Tetrahedron Lett., 3151 (1976)) have shown that for 2-sulphides of the tetrahydropyrano [2,3,e]-1,3,2-dioxaphosphorinan system, the extent to which HS is eliminated depends upon conformation of the thiophosphoryl group
  • Cooks , R. G. and Gerrard , A. F. 1968 . J. Chem. Soc., B , : 1327
  • Data for this compound are not included here but they agree with data already published

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