Dialkoxy disulfides and their branch-bonded thionosulfite isomers

Journal of Sulfur Chemistry

Volumn 25, Issue 2-3, 2004, Pages 155-182

  Zysman Colman, Eli ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Dialkoxy disulfides; Synthesis and characterization; Thermochemistry; Thionosulfite isomers

Indexed keywords

SULFUR COMPOUNDS;

DIALKOXY DISULFIDES; HISTORICAL REVIEW; SYNTHESIS AND CHARACTERIZATIONS; THIONOSULPHITE ISOMER;

ISOMERS;

CHALCOGEN; DISULFIDE; SULFITE; THIONOSULFITE; UNCLASSIFIED DRUG;

CHEMICAL BOND; CHEMICAL REACTION; ISOMER; PHYSICAL CHEMISTRY; REVIEW; SYNTHESIS; THERMAL ANALYSIS;

EID: 3242663398     PISSN: 17415993     EISSN: None     Source Type: Journal    
DOI: 10.1080/1741599342000202176     Document Type: Review

References (107)

1. Lengfeld, F., 1895, Ber., 28, 449.
2. Thompson, Q. E., Crutchfield, M. M. and Dietrich, M. W., 1964, J. Am. Chem. Soc., 86, 3891.
3. Thompson, Q. E., Crutchfield, M. M., Dietrich, M. W. and Pierron, E., 1965, J. Org. Chem., 30, 2692.
4. For a review of Thompson's work on dialkoxy disulfides see: Thompson, Q. E., 1970, Quarterly Rep. Sulf. Chem., 5, 245.
5. Zinner, G., 1957, Angew. Chem., 69, 508.
6. Meuwsen, A., 1935, Ber., 68, 121.
7. Clow, A., Kirton, H. M. and Thompson, J. M. C., 1940, Trans. Farady Soc., 36, 1029.
8. Meuwsen, A., 1936, Ber., 69, 935.
9. Goehring, M. and Stamm, H., 1948, Angew. Chem., A60, 147.
10. Stoll, O. and Scheibe, G., 1938, Ber., 71, 1571.
11. Goehring, M., 1947, Chem. Ber., 80, 219.
12. For a background on the causes of pyramidal inversion see: Mislow, K., Rauk, A. and Allen, L. C., 1970, Angew. Chem. Int. Ed. Engl., 9, 400.
13. For a review on linear free energy correlations of barriers to pyramidal inversion see: Mislow, K., Baechler, R. D., Andose, J. D. and Stackhouse, J., 1972, J. Am. Chem. Soc., 94, 8060.
14. For a review on calculated and experimental barriers to pyramidal inversion for first- and second-row elements see: Mislow, K., Rauk, A.,Andose, J. D., Frick, W. G. and Tang, R., 1971, J. Am. Chem. Soc., 93, 6507.
15. Pritchard, J. G. and Lauterbur, P. C., 1961, J. Am. Chem. Soc., 83, 2105.
16. Faucher, H., Guimaraes, A. C., Robert, J. B., Sauriol, F. and St-Jacques, M., 1981, Tetrahedron, 37, 689.
17. Lauterber, P. C., Pritchard, J. G. and Vollmer, R. L., 1963, J. Chem. Soc., 5307.
18. Baw, H., Bennett, G. M. and Deams, P., 1934, J. Chem. Soc., 680.
19. Fries, K. and Vogt, W., 1911, Ber., 44, 756.
20. Johnson, C. R. and McCants, Jr., D., 1965, J. Am. Chem. Soc., 87, 1109.
21. Johnson, C. R. and McCants, Jr., D., 1964, J. Am. Chem. Soc., 86, 2935.
22. Mislow, K., 1971, Int J. Sulf. Chem. A, 1, 66.
23. Mislow, K., Schneider, P. and Ternay, Jr., A. L., 1964, J. Am. Chem. Soc., 86, 2957.
24. Farina, G., Montanari, F. and Negrini, A., 1959, Gazz. Chim. Ital., 89, 1548.
25. Henbest, H. B. and Khan, S. A., 1964, Proc. Chem. Soc., 56.
26. Mislow, K., Rayner, D. R., Miller, E. G., Bickart, P. and Gordon, A. J., 1966, J. Am. Chem. Soc., 88, 3138.
27. For a detailed investigation into the mechanism and activation parameters of pyramidal inversion of sulfoxides see: Mislow, K., Rayner, D. R. and Gordon, A. J., 1968, J. Am. Chem. Soc., 90, 4854.
28. Thompson, Q. E., 1965, J. Org. Chem., 30, 2703.
29. Claeson, G., Androes, G. and Calvin, M., 1961, J. Am. Chem. Soc., 83, 4357.
30. Steudel, R. and Miaskiewicz, K., 1991, J. Chem. Soc., Dalton Trans., 2395.
31. Steudel, R., Schmidt, H., Baumeister, E., Oberhammer, H. and Koritsanszky, T., 1995, J. Phys. Chem., 99, 8987.
32. Koritsanszky, T., Buschmann, J., Schmidt, H. and Steudel, R., 1994, J. Phys. Chem., 98, 5416.
33. Borghi, R., Lunazzi, L., Placucci, G., Cerioni, G., Foresti, E. and Plumitallo, A., 1997, J. Org. Chem., 62, 4924.
34. Cerioni, G. and Plumitallo, A., 1998, Org. Magn. Resonan., 36, 461.
35. Harpp, D. N., Tardif, S. L. and Williams, C. R., 1995, J. Am. Chem. Soc., 117, 9067.
36. Snyder, J. P., Nevins, N., Tardif, S. L. and Harpp, D. N., 1997, J. Am. Chem. Soc., 119, 12685.
37. Chapman, J. S. and Ghosh, T., 1999, Pat. # EP 1008 296 AI, Europe, 10.
38. For a review on compounds containing the S=S bond see: Turnbull, K. and Kutney, G. W., 1982, Chem. Rev., 82, 333.
39. Foss, O., 1950, Acta Chem. Scand., 4, 404.
40. Harpp, D. N., Steliou, K. and Cheer, C. J., 1980, J. Chem. Soc. Chem. Commun., 825.
41. Harpp, D. N., Zysman-Colman, E. and Abrams, C. B., 2003, J. Org. Chem., 68, 7059.
42. Tanaka, S., Sugihara, Y., Sakamoto, A., Ishii, A. and Nakayama, J., 2003, J. Am. Chem. Soc., 125, 9024.
43. Ligroin is any petroleum distillate fraction wherein its boiling point is below 150°C. Common names for Ligroin include benzine, mineral spirits, and VM&P naphtha though the term ligroin has been used as a substitute for petroleum ether and naphtha.
44. Stamm, H. and Wintzer, H., 1937, Ber., 70, 2058.
45. Hacklin, H., Baltruschat, E. and Röschenthaler, G.-V., 1985, Z. Anorg. Allg. Chem., 522, 155.
46. Wang, C. S., Pullen, K. E. and Shreeve, J. N. M., 1970, Inorg. Chem., 9, 90.
47. Denham, W. S. and Woodhouse, H., 1913, J. Chem. Soc., 1861.
48. Thompson, Q. E., 1968, Pat. # 3,376,322, United States, 8.
49. Borghi, R., Lunazzi, L., Placucci, G., Cerioni, G. and Plumitallo, A., 1996, J. Org. Chem., 61, 3327.
50. Harpp, D. N., Priefer, R. and Farrell, P. G., 2002, Tetrahedron Lett., 43, 8781.
51. Tardif, S., 1997, PhD thesis, McGill University.
52. Braverman, S. and Pechenick, T., 2002, Tetrahedron Lett., 43, 499.
53. Braverman, S., Pechenick, T. and Gottlieb, H. E., 2003, Tetrahedron Lett., 44, 777.
54. Su, Y. Z. and Gong, K. C., 2000, Mater. Res. Soc. Symp. Proc., 600, 215.
55. Röschenthaler, G.-V. and Storzer, W., 1978, Phosphorus Sulf., 4, 373.
56. Harpp, D. N. and Zysman-Colman, E., 2003, J. Org. Chem., submitted.
57. Steudel, R., Göbel, T., Schmidt, H. and Holdt, G., 1989, Fresenius Z. Anal. Chem., 334, 266.
58. Möckel, H. J. and Singer, E., 1989, Chromatographia, 27, 27.
59. Möckel, H. J. and Singer, E., 1990, J. Liquid Chromatogr., 13, 1499.
60. Blaschette, A., Näveke, M. and Jones, P. G., 1991, Z. Naturforsch. B, 46, 5.
61. Harpp, D. N., Steliou, K. and Chan, T. H., 1978, J. Am. Chem. Soc., 100, 1222.
62. Wenschun, E. and Ritzel, R., 1986, Sulf. Lett., 4(5), 161.
63. Harpp, D. N., Nevins, N., Snyder, J. P. and Zysman-Colman, E. Manuscript in preparation.
64. Thompson, Q. E., Crutchfield, M. M. and Dietrich, M. W., 1965, J. Org. Chem., 30, 2696.
65. Price, C. C. and Berti, G., 1954, J. Am. Chem. Soc., 76, 1211.
66. Foss, O., 1961. In: Organic Sulfur Compounds, Kharasch, N. (Ed.) (New York: Pergammon Press), Vol. 1, p. 75.
67. Kuczkowski, R. L. and Wilson, Jr., E. B., 1963, J. Am. Chem. Soc., 85, 2028.
68. Kuczkowski, R. L., 1964, J. Am. Chem. Soc., 86, 3617.
69. Myers, R. J. and Meschi, D. J., 1959, J. Mol. Spectrosc., 3, 405.
70. Meyer, B., Jensen, D. and Oommen, T., 1972. In: Sulfur in Organic and Inorganic Chemistry, Senning, A. (Ed.) (New York: Dekker), Vol. 2, p. 13.
71. Iwasaki, F., 1979, Acta Crystallogr. Sect. B, 35, 2099.
72. Chivers, T., Oakley, R. T., Cordes, A. W. and Swepston, P., 1980, J. Chem. Soc., Chem. Commun., 1, 35.
73. Lovas, F. J., Tiemann, E. and Johnson, D., 1974, J. Chem. Phys., 60, 5005.
74. Marsden, C. J., Oberhammer, H., Losking, O. and Willner, H., 1989, J. Mol. Struct., 193, 233.
75. Steudel, R., Schmidt, H., Sülzle, D. and Schwarz, H., 1992, Inorg. Chem., 31, 941.
76. Using NRMS, HOSSOH is stable for only 10-5 s under highly dilute conditions in the gas phase.
77. Steudel, R. and Schmidt, H., 1990, Z. Naturforsch. Teil B, 45, 557.
78. 2S=O. See: Wallmeier, H. and Kutzelnigg, W., 1979, J. Am. Chem. Soc., 101, 2804.
79. Steudel, R., Gleiter, R., Hyla-Kryspin, I. and Schmidt, H., 1993, Chem. Ber., 126, 2363.
80. Harpp, D. N., Zysman-Colman, E., Nevins, N. and Snyder, J. P., 2003, Manuscript in preparation.
81. Fraser, R. R., Boussard, G., Saunders, J. K. and Lambert, J. B., 1971,J. Am. Chem. Soc., 93, 3822.
82. Seel, F., Gombler, W. and Budenz, R., 1970, Liebigs Ann. Chem., 735, 1.
83. Miscallef, A. S. and Bottle, S. E., 1997, Tetrahedron Lett., 38, 2303.
84. Borghi, R., Guidi, B., Placucci, G. and Lunazzi, L., 1996, J. Org. Chem., 61a, 5667.
85. Braverman, S. and Stabinsky, Y., 1967, J. Chem. Soc., Chem. Commun., 270.
86. Block, E., 1992, Angew. Chem. Int. Ed. Engl., 31, 1135.
87. Braverman, S., Pechenick, T., Gottlieb, H. E. and Sprecher, M., 2003, J. Am. Chem. Soc., 125, 14290.
88. Kobayashi, M., Minato, H. and Shimada, K., 1971, Int. J. Sulf. Chem. A, 1, 105.
89. 18 experiments indicate that the oxygen in sulfite 79 did not arise from thus source.
90. Motoki, S., Kagami, H. and Satsumabayashi, H., 1977, J. Org. Chem., 42, 958.
91. Motoki, S. and Kagami, H., 1977, J. Org. Chem., 42, 4139.
92. Steudel, R. and Schmidt, H., 1994, Chem. Ber., 127, 1219.
93. Motoki, S. and Kagami, H., 1979, Bull. Chem. Soc. Jpn., 52, 3463.
94. Hey, D. H. and Waters, W. A., 1948, J. Chem. Soc., 882.
95. Harpp, D. N., Sawayama, A. M. and Lesté-Lassere, P., 2000, Sulf. Lett., 23, 163.
96. Motoki, S., Kagami, H., Hanzawa, T, Suzuki, N., Yamaguchi, S. and Saito, M., 1980, Bull. Chem. Soc. Jpn., 53, 3658.
97. Ghosh, T. and Bartlett, P. D., 1988, J. Am. Chem. Soc., 110, 7499.
98. Braverman, S. and Pechenick, T., 2003, Synthesis, 2079.
99. Hoepping, A. and Mayer, R., 1994, Bull. Soc. Chim. Belg., 103, 389.
100. Hoepping, A. and Mayer, R., 1995, Phosphorus, Sulf. Silicon, 1-7, 285.
101. Smith, J. D. and O'Hair, R. A. J., 1997, Phosphorus, Sulf. Silicon Relat. Elements, 126, 257.
102. Meuwsen, A. and Gebhardt, H., 1936, Ber., 69, 937.
103. Meuwsen, A. and Gebhardt, H., 1935, Ber., 68, 1011.
104. Matsuyama, H., Minato, H. and Kobayashi, M., 1973, Bull. Chem. Soc. Jpn., 46, 2845.
105. Matsuyama, H., Minato, H. and Kobayashi, M., 1973, Bull. Chem. Soc. Jpn., 46, 3158.
106. Matsuyama, H., Minato, H. and Kobayashi, M., 1973, Bull. Chem. Soc. Jpn., 46, 3828.
107. Trost, B. M., 1967, J. Am. Chem. Soc., 89, 138.