Isonitriles as source and fate of imidoyl radicals: A novel homolytic α-fragmentation

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9337-9340

  Nanni, Daniele ^a   Pareschi, Patrizia ^a   Tundo, Antonio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ISONITRILE DERIVATIVE; NITRILE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82958-9     Document Type: Article

References (30)

1. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
2. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
3. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
4. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
5. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
6. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
7. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
8. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
9. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
10. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
11. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
12. 1. Shaw, D. H.; Pritchard, H. O Canad. J. Chem. 1967, 45, 2749. Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc. 1968, 90, 4182. Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118. Banks, R. E.; Haszeldine, R. N.; Stephens, C. W. Tetrahedron Lett. 1972, 3699. Singer, L. A.; Kim, S. S. Tetrahedron Lett. 1974, 861. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535. Kim, S. S. Tetrahedron Lett. 1977, 2741. Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 209. Meier, M.; Rüchardt, C. Tetrahedron Lett. 1983, 24, 4671. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. Wirth, T.; Rüchardt, C. Chimia 1988, 42, 230. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
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14. 3. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. Curran, D. P.; Josien, H.; Ko, S.-B. Angew. Chem. Int. Ed. 1995, 34, 2683. Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385.
15. 3. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. Curran, D. P.; Josien, H.; Ko, S.-B. Angew. Chem. Int. Ed. 1995, 34, 2683. Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385.
16. 3. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. Curran, D. P.; Josien, H.; Ko, S.-B. Angew. Chem. Int. Ed. 1995, 34, 2683. Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385.
17. 4. Fukuyama, T.; Xiaoqi, C.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127.
18. 5. Bachi, M. D.; Balanov, A.; Bar-Ner, N. J. Org. Chem. 1994, 59, 7752.
19. 6. Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320.
20. Leardini, R.; Tundo, A.; Zanardi, G.; Pedulli, G. F. Synthesis 1985, 107. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans, 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
21. Leardini, R.; Tundo, A.; Zanardi, G.; Pedulli, G. F. Synthesis 1985, 107. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans, 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
22. Leardini, R.; Tundo, A.; Zanardi, G.; Pedulli, G. F. Synthesis 1985, 107. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans, 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
23. Leardini, R.; Tundo, A.; Zanardi, G.; Pedulli, G. F. Synthesis 1985, 107. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans, 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
24. 7. Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045.
25. 1H-NMR, MS, and HRMS data.
26. 9. A GC-MS analysis of the reaction mixture showed small amounts of 2-phenylprop-2-yl iso-propyl ether, acetophenone, 2-phenylpropan-2-ol, α-methylstyrene, and 2,2-diphenylpropane, which were identified by comparison with the authentic spectra contained in the instrument database. The same products were also obtained, in the same ratio, by reacting cumene with DPDC under the same conditions.
27. 10. A GC-MS analysis of the reaction mixture showed the presence of triphenylmethyl iso-propyl ether, benzophenone, triphenylmethanol, triphenylmethane, and tetraphenylmethane. The same products were also detected in the reactions of triphenylmethane with DPDC, both in the presence and in the absence of 1, under the same conditions.
28. 11. This ratio was obtained after 40 min, when some starting material was still present. After 4 h only small amounts of 14 were detected, but the yield of 17 dropped to 5% and a GC-MS analysis of the crude showed major amounts of other products containing the dodecyl moiety. Isonitrile 17 is clearly unstable under the reaction conditions and, probably, the actual 17/16 ratio is much higher than that experimentally obtained.
29. 12. Barton, D. H. R.; Bringmann, G.; Lamotte, G.; Motherwell, W. B.; Motherwell, R. S. H.; Porter, A. E. A. J. Chem. Soc., Perkin Trans. I 1980, 2657.
30. 12. Barton, D. H. R.; Bringmann, G.; Lamotte, G.; Motherwell, W. B.; Motherwell, R. S. H.; Porter, A. E. A. J. Chem. Soc., Perkin Trans. I 1980, 2657. Bachi, M.D.; Denenmark, D. J. Org. Chem. 1990, 55, 3442.