Preparation and reactivity of 1,3-bis(alkylthio)allenes and tetrathiacyclic bisallenes

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1721-1728

  Shimizu, Toshio ^a   Sakamaki, Kensuke ^a   Miyasaka, Daisuke ^a   Kamigata, Nobumasa ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; BENZOTHIEPIN DERIVATIVE; CYCLOBUTANE DERIVATIVE; DIAZOMETHANE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; SULFUR; THIOCYANIC ACID DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; IRRADIATION; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0034708451     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9915675     Document Type: Article

References (66)

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27. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
28. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
29. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
30. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
31. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
32. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
33. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
34. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
35. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
36. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
37. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
38. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
39. For examples, see: (a) Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1249; Chem. Abstr. 1914, 8, 320. (b) Blomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1956, 78, 109. (c) Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 4269. (d) Pilgram, K.; Korte, F. Tetrahedron Lett. 1962, 883. (e) Roedig, A.; Bischoff, F.; Heinrich, B.; Markl, G. Ann. Chem. 1963, 670, 8. (f) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 146. (g) Slobodin, Y. M.; Khitrov, A. P. J. Gen. Chem. USSR 1963, 33, 2748. (h) Roedig, A.; Detzer, N.; Friedrich, H. J. Angew. Chem. 1964, 76, 379. (i) Fischer, H.; Fischer, H. Chem. Ber. 1964, 97, 2975. (j) Banks, R. E.; Haszeldine, R. N.; Taylor, D. R. J. Chem. Soc. 1965, 978. (k) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506. (l) Gajewski, J. J.; Shih, C. N. J. Am. Chem. Soc. 1969, 91, 5900. (m) Jacobs, T. L.; McClenon, J. R.; Muscio, O. J., Jr. J. Am. Chem. Soc. 1969, 91, 6038. (n) Gajewski, J. J.; Black, W. A. Tetrahedron Lett. 1970, 899. (o) Jacobs, T. L.; Muscio, O. J., Jr. Tetrahedron Lett. 1970, 4829. (p) Dolbier, W. R., Jr.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774. (q) Gajewski, J. J.; Shih, C. N. J. Org. Chem. 1972, 37, 64. (r) Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3946.
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