Two carbon homologation of carboxylic acids using acrylamide as a radical trap

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2431-2434

  Barton, Derek H R ^a   Liu, Wansheng ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DESULFURIZATION; DRUG SYNTHESIS; PHOTOLYSIS;

EID: 0030936001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00418-8     Document Type: Article

References (27)

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2. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Baldwin, J.E. Ser. Ed.; Pergamon Press: Oxford, 1986. Curran, D.P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996.
3. Barton, D.H.R.; Zard, S.Z. Janssen Chimica Acta 1987, 4, 3. Barton, D.H.R. Tetrahedron 1992, 48, 2529. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035. Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
4. Barton, D.H.R.; Zard, S.Z. Janssen Chimica Acta 1987, 4, 3. Barton, D.H.R. Tetrahedron 1992, 48, 2529. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035. Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
5. Barton, D.H.R.; Zard, S.Z. Janssen Chimica Acta 1987, 4, 3. Barton, D.H.R. Tetrahedron 1992, 48, 2529. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035. Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
6. Barton, D.H.R.; Zard, S.Z. Janssen Chimica Acta 1987, 4, 3. Barton, D.H.R. Tetrahedron 1992, 48, 2529. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035. Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
7. Barton, D.H.R.; Zard, S.Z. Janssen Chimica Acta 1987, 4, 3. Barton, D.H.R. Tetrahedron 1992, 48, 2529. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron 1985, 41, 3901. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035. Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
8. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753. Barton, D.H.R.; Boivin, J.; Crépon, E.; Sarma, J.; Togo, H.; Zard, S.Z. Tetrahedron 1991, 47, 7091. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Aust. J. Chem. 1995, 48, 407.
9. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753. Barton, D.H.R.; Boivin, J.; Crépon, E.; Sarma, J.; Togo, H.; Zard, S.Z. Tetrahedron 1991, 47, 7091. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Aust. J. Chem. 1995, 48, 407.
10. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753. Barton, D.H.R.; Boivin, J.; Crépon, E.; Sarma, J.; Togo, H.; Zard, S.Z. Tetrahedron 1991, 47, 7091. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Aust. J. Chem. 1995, 48, 407.
11. Barton D.H.R., Chern C.-Y., Jaszberenyi J.Cs. Tetrahedron Lett. 32:1991;3309.
12. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Tetrahderon Lett. 1992, 33, 5017. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Tetrahderon 1995, 51, 1867.
13. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Tetrahderon Lett. 1992, 33, 5017. Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J. Cs. Tetrahderon 1995, 51, 1867.
14. Larock, R.C. Comprehensive Organic Transformations; VCH: New York, 1989; pp. 988-993. For a recent conversion of primary amides to nitriles, see: Heck, M.-P.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1996, 61, 6486.
15. Larock, R.C. Comprehensive Organic Transformations; VCH: New York, 1989; pp. 988-993. For a recent conversion of primary amides to nitriles, see: Heck, M.-P.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1996, 61, 6486.
16. Barton D.H.R., Samadi M. Tetrahedron. 48:1992;7083. and references there cited.
17. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
18. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
19. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
20. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
21. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
22. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
23. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
24. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
25. Schlesinger, H.I.; Brown, H.C.; Finholt, A.E.; Gilbreath, J.R.; Hoekstra, H.R.; Hyde, E.K. J. Am. Chem. Soc. 1953, 75, 215. Brown, C.A.; Brown, H.C. J. Am. Chem. Soc., 1963, 85, 1003. Brown, H.C.; Brown, C.A. J. Am. Chem. Soc., 1963, 85, 1005. Brown, C.A. Chem. Commun. 1969, 952. Brown, C.A. J. Org. Chem. 1970, 35, 1900. Truce, W.E.; Roberts, F.E. J. Org. Chem. 1963, 28, 961. Truce, W.E.; Perry, F.M. J. Org. Chem. 1965, 30, 1316. Boar, R.B.; Hawkins, D.W.; McGhie, J.F.; Barton, D.H.R. J. Chem. Soc., Perkin Trans. I 1973, 654. Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M.A. J. Org. Chem. 1994, 59, 7934.
26. Cavalieri L., Pattison D.B., Carmack M. J. Am. Chem. Soc. 67:1945;1783. In this reference, compound 5a was synthesized in 27% yield by a Willgerodt reaction from cyclohexyl ethyl ketone.
27. Barton D.H.R., Jaszberenyi J. Cs, Liu W., Shinada T. Tetrahedron. 52:1996;2717.