Synthesis and synthetic application of phosphonoketene dithioacetals. New synthesis of dithioallenes and (α-dithiocarboxyvinyl)phosphonates

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8132-8140

  Minami, Toru ^a   Okauchi, Tatsuo ^a   Matsuki, Hiroyasu ^a   Nakamura, Mitsuharu ^a   Ichikawa, Junji ^a   Ishida, Masaru ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIOLANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE; X RAY ANALYSIS;

EID: 0029827951     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960491z     Document Type: Article

References (39)

1. For reviews of ketene dithioacetals, see: (a) Kolb, M. Synthesis 1990, 71. (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
2. For reviews of ketene dithioacetals, see: (a) Kolb, M. Synthesis 1990, 71. (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
3. For a review of vinylphosphonates, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
4. For the synthesis of diphenylphosphorylketene and phosphonoketene dithioacetals, see: (a) Schaumann, E.; Grabley, F. F. Liebigs Ann. Chem. 1979, 1715. (b) Schaumann, E.; Fittkau, S. Bull. Soc. Chim. Belg. 1985, 94, 462. (c) Schaumann, E.; Fittkau, S. Synthesis 1983, 449.
5. For the synthesis of diphenylphosphorylketene and phosphonoketene dithioacetals, see: (a) Schaumann, E.; Grabley, F. F. Liebigs Ann. Chem. 1979, 1715. (b) Schaumann, E.; Fittkau, S. Bull. Soc. Chim. Belg. 1985, 94, 462. (c) Schaumann, E.; Fittkau, S. Synthesis 1983, 449.
6. For the synthesis of diphenylphosphorylketene and phosphonoketene dithioacetals, see: (a) Schaumann, E.; Grabley, F. F. Liebigs Ann. Chem. 1979, 1715. (b) Schaumann, E.; Fittkau, S. Bull. Soc. Chim. Belg. 1985, 94, 462. (c) Schaumann, E.; Fittkau, S. Synthesis 1983, 449.
7. For the Wittig reaction of [bis(alkylthio)vinylidene]triphenyl phosphoranes with a reactive carbonyl reagent, diphenylketene, see: Bestmann, H. J.; Roth, K. Tetrahedron Lett. 1981, 22, 1681.
8. For the synthesis of ketene dithioacetals using dithiol-trimethylaluminum, see: Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1973, 95, 5829.
9. 3Si (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977, 110, 867. For RS, see ref 7b. (c) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For RSe, see ref 7b. For a review of synthesis and synthetic application of α-seleno and α-telluro vinylcarbanions, see: (d) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
10. 3Si (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977, 110, 867. For RS, see ref 7b. (c) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For RSe, see ref 7b. For a review of synthesis and synthetic application of α-seleno and α-telluro vinylcarbanions, see: (d) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
11. 3Si (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977, 110, 867. For RS, see ref 7b. (c) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For RSe, see ref 7b. For a review of synthesis and synthetic application of α-seleno and α-telluro vinylcarbanions, see: (d) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
12. 3Si (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977, 110, 867. For RS, see ref 7b. (c) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For RSe, see ref 7b. For a review of synthesis and synthetic application of α-seleno and α-telluro vinylcarbanions, see: (d) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
13. Macomber, R. S.; Hemling, C. S. J. Am. Chem. Soc. 1986, 108, 343.
14. There is no unambiguous proof that 3a opens to 9b.
15. For the synthesis of 1,1-(dialkylthio)-1,2-propadienes, see: (a) Clinet, J. C.; Julia, S. J. Chem. Res. (M) 1978, 1714. (b) Saalfrank, R. W. Isr. J. Chem. 1985, 26, 181.
16. For the synthesis of 1,1-(dialkylthio)-1,2-propadienes, see: (a) Clinet, J. C.; Julia, S. J. Chem. Res. (M) 1978, 1714. (b) Saalfrank, R. W. Isr. J. Chem. 1985, 26, 181.
17. For the cyclodimerization of alienes, see: Pasto, D. J. J. Am. Chem. Soc. 1979, 101, 37.
18. w = 0.039.
19. w = 0.033. The authors have deposited the atomic coordinates for the structures of 20 and 23b with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
20. Purification of the dithioallene 26 on silica gel was difficult due to the ease of hydrolysis.
21. Dithio allenes are labile and difficult to be isolated; e.g., 1,1-bis(methylthio)-3,3-dimethyl-1,2-propadiene, which is prepared by the reaction of 1-lithio-3-chloro-3-methyl-1-butyne and dimethyl disulfide, is isomerized on silica gel into 1,1-bis(methylthio)-3-methyl-1,3-buta-diene, see ref 9a.
22. For the [2 + 2] cycloaddition reaction between ketene and allene, see: (a) Bertrand, M.; Maurin, R.; Gras, J. L.; Gil, G. Tetrahedron 1975, 31, 849. (b) Bertrand, M.; Gras, J. L.; Gore, J. Tetrahedron 1975, 31, 857. For ab initio studies on the mechanism of the cycloaddition between ketene and allene, see: (c) Fang, D. C.; Fu, X. Y. Int. J. Quant. Chem. 1994, 50, 93.
23. For the [2 + 2] cycloaddition reaction between ketene and allene, see: (a) Bertrand, M.; Maurin, R.; Gras, J. L.; Gil, G. Tetrahedron 1975, 31, 849. (b) Bertrand, M.; Gras, J. L.; Gore, J. Tetrahedron 1975, 31, 857. For ab initio studies on the mechanism of the cycloaddition between ketene and allene, see: (c) Fang, D. C.; Fu, X. Y. Int. J. Quant. Chem. 1994, 50, 93.
24. For the [2 + 2] cycloaddition reaction between ketene and allene, see: (a) Bertrand, M.; Maurin, R.; Gras, J. L.; Gil, G. Tetrahedron 1975, 31, 849. (b) Bertrand, M.; Gras, J. L.; Gore, J. Tetrahedron 1975, 31, 857. For ab initio studies on the mechanism of the cycloaddition between ketene and allene, see: (c) Fang, D. C.; Fu, X. Y. Int. J. Quant. Chem. 1994, 50, 93.
25. MOPAC Ver. 6, Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Revised as Ver. 6.01 by Hirano, T., University of Tokyo, for HITAC and UNIX machines, JCPE Newsletter 1980, 1, 10.
26. MOPAC Ver. 6, Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Revised as Ver. 6.01 by Hirano, T., University of Tokyo, for HITAC and UNIX machines, JCPE Newsletter 1980, 1, 10.
27. Minami, T.; Utsunomiya, T.; Nakamura, S.; Okubo, M.; Kitamura, N.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1994, 59, 6717.
28. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
29. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
30. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
31. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
32. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
33. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
34. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
35. For a review of dithiocarboxylic acid esters (dithioesters), see: (a) Kato, S.; Ishida, M. Sulfur Rep. 1988, 8(4), 155. For the synthesis of dithioester (non α, β-olefinic) via ketene dithioacetal, see for example: (b) Beslin, P.; Perrio, S. Phosphorus Sulfur Silicon Relat. Elem. 1994, 95 and 96, 383. (c) Saquet, M.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2165. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. J. Org. Chem. 1983, 48, 4795. (e) Ogura, K.; Itoh, Y.; Tsuchihashi, G. Synthesis 1980, 736. For the synthesis of áâ-unsaturated dithioesters, see for example: (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2717. (g) Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960. (h) Masson, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
36. For the synthesis of 3H-cyclopenta[α]pyrrole-2-carboxylate via similar reaction of α-phosphonoacrylates with pyrrole-2-carbaldehyde, see: (a) Minami, T.; Suganuma, H.; Agawa, T. Chem. Lett. 1978, 285. (b) Flitsch, W.; Lubisch, W. Chem. Ber. 1984, 117, 1424.
37. For the synthesis of 3H-cyclopenta[α]pyrrole-2-carboxylate via similar reaction of α-phosphonoacrylates with pyrrole-2-carbaldehyde, see: (a) Minami, T.; Suganuma, H.; Agawa, T. Chem. Lett. 1978, 285. (b) Flitsch, W.; Lubisch, W. Chem. Ber. 1984, 117, 1424.
38. (a) Kametani, T.; Takahashi, K. Heterocycles 1978, 9, 293.
39. (b) Franck, R. W. Fortschr. Chem. Org. Naturst. 1979, 38, 1.