Thion (RCSOH), selenon (RCSeOH), and telluron (RCTeOH) acids as predominant species

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1262-1267

  Kato, Shinzi ^a   Kawahara, Yasuyuki ^a   Kageyama, Hideki ^a   Yamada, Ryo ^a   Niyomura, Osamu ^a   Murai, Toshiaki ^a   Kanda, Takahiro ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ORGANOSELENIUM DERIVATIVE; ORGANOTELLURIUM DERIVATIVE; THIOACID;

ARTICLE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 0029882817     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953035l     Document Type: Article

References (63)

1. (a) Bauer, W.; Khüren, K. In Methoden der Organischen Chemie, 5th ed.; Falbe, J., Ed.; Georg Thieme Publishers: Stuttgart, Germany, 1985; pp 832-890.
2. (b) Abeles, R. H.; Frey, P. A.; Jencks, W. P. Biochemistry; Jones and Bartlett: Boston, MA, 1992.
3. (c) Ishii, Y.; Nakayama, J. In Organic Functional Group Transformations; Rees, C. W., Ed.; Pergamon Press: New York. 1995; Vol. 5, Chapter 5.12.
4. Kekulé, A. Ann. Chem. Pharm. 1854, 90, 309.
5. 6q) are not based on unambiguously assigned bands.
6. Kageyama, H.; Murai, T.; Kanda, T.; Kato, S. J. Am. Chem. Soc. 1994, 116, 2195.
7. Murthy, A. S. N.; Rao, C. N. R.; Rao, B. D. N.; Venkateswarhu, P. Trans. Faraday Soc. 1962, 58, 855.
8. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
9. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
10. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
11. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
12. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
13. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
14. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
15. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
16. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
17. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
18. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
19. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
20. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
21. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
22. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
23. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
24. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
25. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
26. For infrared, see: (a) Kohlrausch, K. W. F.; Pongratz, A. Z. Phyz. Chem. B 1934, 27, 176. (b) Sheppard, N. Trans. Faraday Soc. 1949, 45, 693. (c) Crouch, W. W. J. Am. Chem. Soc. 1952, 74, 2926. (d) Mecke, R.; Spiesecke, H. Chem. Ber. 1956, 89, 1110. (e) Sjöberg, B. Acta Chem. Scand. 1957, 11, 945. (f) Nyquest, R. A.; J. Potts, W. Spectrochim. Acta 1959, 15, 514. (g) Ginzburg, I. M.; Loginova, L. A. Opt. Spectrom. 1966, 20, 130. (h) Engler, V. R.; Gattow, G. Z. Anorg. Allg. Chem. 1972, 388, 78. (i) Beumer, A. E.; Harkema, S. Acta Crystallogr. 1973, B29, 682. (j) Bicca de Alencastro, R.: Sandorfy, C. Can. J. Chem. 1973, 51, 1443. (k) Crowder, G. A. Appl. Spectrosc. 1973, 27, 440. (l) Randhawa, H. S.; Rao, C. N. R. J. Mol. Struct. 1974, 21, 123. (m) Crowder, G. A.; Robertson, E.; Potter, K. Can. J. Spectrosc. 1975, 20, 49. (n) Crowder, G. J. Mol. Struct. 1976, 32, 207. (o) Randhawa, H. S.; Meese, C. O.; Walter, W. J. Mol. Struct. 1977, 36, 25. (p) Randhawa, H. S.; Walter, W. J. Mol. Struct. 1977, 38, 89. For UV/vis, see: (q) Sheinker, Yu N.; Ioffe, S. T.; Kabachnik, M. Izv. Akad. Nauk. SSSR., Otd. Khim. Nauk. 1960, 1571 (English Transl. p 1463). (r) Nagata, S.; Yamabe, T.; Fukui, K. J. Phys. Chem. 1975, 79, 2335. (s) Yamabe, T.; Akagi, K.; Nagata, S.; Kato, H.; Fukui, K. J. Phys. Chem. 1976, 80, 611. For NMR. see refs 6a,b.
27. (a) Holmberg, B. Ark. Kemi, Mineral. Geol. 1938, 12B, No. 47.
28. (b) Holmberg, B.; Schjinberg, C. Ark. Kemi, Mineral. Geol. 1940, 14A, No. 2.
29. (a) Naito, T.; Ohashi, O.; Yamaguchi, I. J. Mol. Spectrosc. 1977. 68, 32.
30. (b) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C. J. Mol. Struct. (THEOCHEM) 1987, 150, 38.
31. For thioformic acid, see: (c) George, P.; Bock, C. W.; Schmiedekamp, A. S. J. Mol. Struct. (THEOCHEM) 1981, 76, 363. (d) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C.; Ramos, V. J. Chem. Soc., Faraday Trans. 1989. 2, 1945. (e) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C. J. Mol. Struct. 1990, 207, 67.
32. For thioformic acid, see: (c) George, P.; Bock, C. W.; Schmiedekamp, A. S. J. Mol. Struct. (THEOCHEM) 1981, 76, 363. (d) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C.; Ramos, V. J. Chem. Soc., Faraday Trans. 1989. 2, 1945. (e) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C. J. Mol. Struct. 1990, 207, 67.
33. For thioformic acid, see: (c) George, P.; Bock, C. W.; Schmiedekamp, A. S. J. Mol. Struct. (THEOCHEM) 1981, 76, 363. (d) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C.; Ramos, V. J. Chem. Soc., Faraday Trans. 1989. 2, 1945. (e) Fausto, R.; Batista de Carbalho, L. A. E.; Teixeira-Dias, J. J. C. J. Mol. Struct. 1990, 207, 67.
34. max (log ∈): 418 (2.20) (hexane) (Ohno, A.; Koizumi, T.; Ohishi, Y.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1969, 42, 3556).
35. 3).
36. 3).
37. 3).
38. 3).
39. 3 = 2.99:3.00).
40. -1, respectively.
41. 6p
42. 5,6g,j have been interpreted in terms of hydrogen-bonded dimers A and B (self-association) in the solid state and in a dilute solution. However, no evidence was obtained, indicating the presence of the cyclic dimer C of a thion acid in a polar solvent such as THF. Further comment on the self-association will be left for the discussion. (Formula Presented)
43. 6b
44. The synthesis and characterization of carbon-chalcogen multiple bond are of current research interest. For review, see: Okazaki, R. J. Synth. Org. Chem. Jpn. 1988, 46, 1149. (b) Usov, V. A.; Timokhina, L. V.; Voronkov, M. G. Sulfur Rep. 1992, 12, 95-158. (d) Guziec, F. S., Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; Vol. 2, pp 215-273. (e) Guziec, F. S., Jr. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; p 77.
45. The synthesis and characterization of carbon-chalcogen multiple bond are of current research interest. For review, see: Okazaki, R. J. Synth. Org. Chem. Jpn. 1988, 46, 1149. (b) Usov, V. A.; Timokhina, L. V.; Voronkov, M. G. Sulfur Rep. 1992, 12, 95-158. (d) Guziec, F. S., Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; Vol. 2, pp 215-273. (e) Guziec, F. S., Jr. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; p 77.
46. The synthesis and characterization of carbon-chalcogen multiple bond are of current research interest. For review, see: Okazaki, R. J. Synth. Org. Chem. Jpn. 1988, 46, 1149. (b) Usov, V. A.; Timokhina, L. V.; Voronkov, M. G. Sulfur Rep. 1992, 12, 95-158. (d) Guziec, F. S., Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; Vol. 2, pp 215-273. (e) Guziec, F. S., Jr. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; p 77.
47. The synthesis and characterization of carbon-chalcogen multiple bond are of current research interest. For review, see: Okazaki, R. J. Synth. Org. Chem. Jpn. 1988, 46, 1149. (b) Usov, V. A.; Timokhina, L. V.; Voronkov, M. G. Sulfur Rep. 1992, 12, 95-158. (d) Guziec, F. S., Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; Vol. 2, pp 215-273. (e) Guziec, F. S., Jr. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; p 77.
48. (a) Kawahara, Y.; Kato, S.; Kanda, T.; Murai, T. Chem. Lett. 1995, 87.
49. (b) Kawahara, Y.; Kato, S.; Kanda, T.; Murai, T.; Ebihara, M. Bull. Chem. Soc. Jpn. 1995, 68, 3507.
50. 3); (c) Severengis, T.; du Mont, W. W. J. Chem. Soc., Chem. Commun. 1987, 820-821].
51. 3); (c) Severengis, T.; du Mont, W. W. J. Chem. Soc., Chem. Commun. 1987, 820-821].
52. 3); (c) Severengis, T.; du Mont, W. W. J. Chem. Soc., Chem. Commun. 1987, 820-821].
53. 18c
54. 17b
55. 13C NMR spectral studies. Presumably the telluride would be formed by detelluration of the corresponding diacyl ditelluride.
56. For the reaction with RCSSH, see: (a) Kato, S.; Mitani, T.; Mizuta, M. Bull. Chem. Soc. Jpn. 1972, 45, 3653. We have postulated an analogous intramolecular six-member-ring structure stabilized by hydrogen-bonding between the thiocarbonyl sulfur and NH hydrogen atoms. For the reaction with RCOSH, see: Motoki, S.; Saito, T.; Kasami, H. Bull. Chem. Soc. Jpn. 1974, 44, 775.
57. For the reaction with RCSSH, see: (a) Kato, S.; Mitani, T.; Mizuta, M. Bull. Chem. Soc. Jpn. 1972, 45, 3653. We have postulated an analogous intramolecular six-member-ring structure stabilized by hydrogen-bonding between the thiocarbonyl sulfur and NH hydrogen atoms. For the reaction with RCOSH, see: Motoki, S.; Saito, T.; Kasami, H. Bull. Chem. Soc. Jpn. 1974, 44, 775.
58. Kageyama, H.; Asada, K.; Maejima, K.; Kanda, T.; Murai, T.; Kato, S. The 67th Spring Annual Meeting of The Japan Chemical Society, Tokyo, Abstr. II, March 1994; p 1320, (4HX-07).
59. Ogawa, T.; Asada, K.; Kageyama, H.; Kanda, T.; Murai, T.; Kato, S. The 69th Spring Annual Meeting of The Japan Chemical Society, Kyoto, Abstr. II, March 1995; p 1304, (2HX-30).
60. (a) Nobel, P. L., Jr.; Tarbel, D. S. Org. Synth. 1963, Collect. Vol. 4, 924.
61. (b) Bloch, I.; Bergmann, M. Ber. Dtsch. Chem. Ges. 1920, 53, 961.
62. (c) Weigert, F. Ber. Dtsch. Chem. Ges. 1903, 36, 1011.
63. The term "under argon" means that the system was evacuated with an oil pump and refilled with argon at least three times and that a positive (ca. 3 Torr) of argon was maintained during the experiment.