Synthetic potentialities of alkyl and aryl cyclopropylidenealkyl sulfides: Access to 1-(arylthio)vinylcyclopropanes by a 1,3-shift of an arylthio group

Synthesis

Volumn , Issue 3, 1996, Pages 361-366

  Bernard, Angela M ^a   Cocco, Maria T ^a   Congiu, Cenzo ^a   Franzone, G Luca ^a   Piras, Pier P ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

cyclopropylidenealkylthioethers; Pd(0) catalyzed allylic nucleophilic substitutions; sulph onium salts; thia allylic rearrangement; vinylcyclopropanes

Indexed keywords

CYCLOPROPANE DERIVATIVE; SULFIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029876127     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4222     Document Type: Article

References (35)

1. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
2. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
3. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
4. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
5. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
6. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
7. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
8. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
9. For some leading references see: Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249. Trost, B. M. Top. Curr. Chem. 1986, 133, 3. Clorembeau, M.; Bertrand, J. L.; Krief, A. Isr. J. Chem. 1984, 24, 125. Trost, B. M.; Cossy, J.; Burks, J. J. Am. Chem. Soc. 1983, 105, 1052. Zutterman, F.; Krief, A. J. Org. Chem. 1983, 48, 1135. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 289 and 5311. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932. Patel, D. J.; Howden, M. E. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
10. Salaun, J. R. Y. Top. Curr. Chem. 1988, 144, 1.
11. Geiss, K.; Seuring, B.; Pieter, R.; Seebach, D. Angew. Chem. 1974, 86, 484; Angew. Chem., Int. Ed. Engl. 1974, 13, 479.
12. Geiss, K.; Seuring, B.; Pieter, R.; Seebach, D. Angew. Chem. 1974, 86, 484; Angew. Chem., Int. Ed. Engl. 1974, 13, 479.
13. Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1, 1973, 654.
14. Trost, B. M.; Keeley, D. E.; Arndt, H. C.; Bogdanowitz, M. J. J. Am. Chem. Soc. 1977, 99, 3088.
15. Trost, B. M.; Jungheim, L. N. J. Am. Chem. Soc. 1980, 102, 7910.
16. Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717.
17. Bernard, A. M.; Piras, P. P. J. Chem. Soc., Chem. Commun. 1994, 257.
18. In the case of (phenylthio)acetaldehyde the reaction was not successful, probably as a consequence of the acidity of the a protons that could favor enolization over condensation.
19. Stafford, A. J.; McMurry, E. J. Tetrahedron Lett. 1988, 29, 2531.
20. Vogeli, U.; von Philipsborn, W. Org. Magn. Reson. 1975, 7, 617.
21. Brownbridge, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1976, 2125; 1977, 2272.
22. Brownbridge, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1976, 2125; 1977, 2272.
23. Kwart, H.; Johnson, N. A. J. Am. Chem. Soc. 1977, 99, 3441.
24. Duhamel, L.; Chauvin, J.; Messier, A. Tetrahedron Lett. 1980, 21, 4171.
25. Werner, E. G. G. Rec. Trav. Chim. Pays-Bas 1949, 68, 519.
26. Newell, O.; Calaway, P. K. J. Am. Chem. Soc. 1947, 69, 116.
27. Ohta, N.; Sudo, R. J. Pharm. Soc. Jpn. 1949, 69, 43.
28. Govindachari, T. R.; Prabhakar, S.; Santhanam, P. S.; Sudrasanam, V. Ind. J. Chem. 1966, 4, 4337.
29. Royer, R.; Demerseman, P.; Lechartier, J. P.; Jantet, A. M. L.; Chentin, A.; Desvoye, M. L. Bull. Soc. Chim. France 1964, 315.
30. Cagniant, P.; Faller, P.; Cagniant, D. Bull. Soc. Chim. Fr. 1966, 3055.
31. Autenrieth, W. Ber. Dtsch. Chem. Ges. 1891, 24, 159.
32. Wahl, C. Ber. Dtsch. Chem. Ges. 1922, 55, 1450.
33. Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1979, 1074.
34. Trost, B. M.; Keeley, D. E. J. Am. Chem. Soc. 1976, 98, 248.
35. Johnson, C. R.; Herr, R. W. J. Org. Chem. 1973, 38, 3153.