Cyclisation of dienes using phosphorus-centred radicals to form organophosphorus adducts

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 479-483

  Jessop, Christopher M ^a   Parsons, Andrew F ^a   Routledge, Anne ^a   Irvine, Derek ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Uniqema   (United Kingdom)

Author keywords

Cyclisation; Dienes; Phosphorus compounds; Radicals and radical reactions

Indexed keywords

ALKADIENE; HETEROCYCLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHITE; PHOSPHORUS DERIVATIVE; RADICAL;

ALLYLATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037433936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02610-2     Document Type: Article

References (43)

1. Bowman W.R., Cloonan M.O., Krintel S.L. J. Chem. Soc., Perkin Trans. 1. 2001;2885-2902.
2. Parsons A.F. An Introduction to Free Radical Chemistry. 2000;Blackwell Science, Oxford.
3. Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. 48:1996;301-856.
4. McCarroll A.J., Walton J.C. J. Chem. Soc., Perkin Trans. 1. 2001;3215-3229.
5. See for example: (a) Hanessian, S.; Reinhold, U.; Ninkovic, S. Tetrahedron Lett. 1996, 37, 8967-8970; (b) Hanessian, S.; Ninkovic, S.; Reinhold, U. Tetrahedron Lett. 1996, 37, 8971-8974; (c) Parsons, A. F.; Williams, D. A. J. Tetrahedron 1998, 54, 13405-13420.
6. See for example: (a) Hanessian, S.; Reinhold, U.; Ninkovic, S. Tetrahedron Lett. 1996, 37, 8967-8970; (b) Hanessian, S.; Ninkovic, S.; Reinhold, U. Tetrahedron Lett. 1996, 37, 8971-8974; (c) Parsons, A. F.; Williams, D. A. J. Tetrahedron 1998, 54, 13405-13420.
7. See for example: (a) Hanessian, S.; Reinhold, U.; Ninkovic, S. Tetrahedron Lett. 1996, 37, 8967-8970; (b) Hanessian, S.; Ninkovic, S.; Reinhold, U. Tetrahedron Lett. 1996, 37, 8971-8974; (c) Parsons, A. F.; Williams, D. A. J. Tetrahedron 1998, 54, 13405-13420.
8. Baguley P.A., Walton J.C. Angew. Chem., Int. Ed. 37:1998;3072-3082.
9. Gilbert B.C., Parsons A.F. J. Chem. Soc., Perkin Trans. 2. 2002;367-387.
10. Studer A., Amrein S. Synthesis. 2002;835-849.
11. Binmore G., Cardellini L., Walton J.C. J. Chem. Soc., Perkin Trans. 2. 1997;757-762.
12. Jackson L.V., Walton J.C. Chem. Commun. 2000;2327-2328.
13. Studer A., Amrein S. Angew. Chem., Int. Ed. 39:2000;3080-3082.
14. Graham S.R., Murphy J.A., Coates D. Tetrahedron Lett. 40:1999;2415-2416.
15. Martin C.G., Murphy J.A., Smith C.R. Tetrahedron Lett. 41:2000;1833-1836.
16. Graham S.R., Murphy J.A., Kennedy A.R. J. Chem. Soc., Perkin Trans. 1. 1999;3071-3073.
17. Kita Y., Nambu H., Ramesh N.G., Anilkumar G., Matsugi M. Org. Lett. 3:2001;1157-1160.
18. Yorimitsu H., Shinokubo H., Oshima K. Bull. Chem. Soc. Jpn. 74:2001;225-235.
19. Yorimitsu H., Shinokubo H., Oshima K. Chem. Lett. 2000;104-105.
20. Reding M.T., Fukuyama T. Org. Lett. 1:1999;973-976.
21. Parsons A.F. Chem. Br. 2002;42-44.
22. Barks J.M., Gilbert B.C., Parsons A.F., Upeandran B. Tetrahedron Lett. 42:2001;3137-3140.
23. Barks J.M., Gilbert B.C., Parsons A.F., Upeandran B. Synlett. 2001;1719-1722.
24. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
25. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
26. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
27. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
28. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
29. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
30. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
31. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
32. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
33. For addition of phosphorus-centred radicals to alkenes, see for example: (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236; (b) Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-7372; (c) Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710; (d) Kenney, R. L.; Fisher, G. S. J. Org. Chem. 1974, 39, 682-686; (e) Callot, H. J.; Benezra, C. Can. J. Chem. 1971, 49, 500-504; (f) Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Aust. J. Chem. 1995, 48, 625-634; (g) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (h) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362; (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200; (j) Nifant'ev, É. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. J. Gen. Chem. USSR (Engl. Transl.) 1991, 61, 83-92.
34. All spectral data were in accord with the structures assigned.
35. 2PH), see: Brumwell J.E., Simpkins N.S., Terrett N.K. Tetrahedron. 50:1994;13533-13552.
36. Bhattacharyna A.K., Thyagarajan G. Chem. Rev. 81:1981;415-430.
37. +, 235.1463).
38. This contrasts with the cyclisation of ethyl diallylacetate (1 equiv.) using diethyl phosphite (1 equiv.), which has been reported to give a mixture of cyclopentane (minor) and cyclohexane (major) products. See: Cadogan, J. I. G.; Hey, D. H.; Hock, A. O. S. Chem. Ind. (London) 1964, 753. The predominant formation of the 6-endo product, in the presence of only 1 equiv. of diethyl phosphite, may be explained by a reversible 5-exo cyclisation. However, in our hands, no organophosphorus adducts were detected when using only 1 equiv. of diethyl phosphite and 5×0.3 equiv. of AIBN.
39. Depréle S., Montchamp J.-L. J. Org. Chem. 66:2001;6745-6755.
40. -1 at 130°C. See: Chatgilialoglu C., Timokhin V.I., Ballestri M. J. Org. Chem. 63:1998;1327-1329.
41. For a related thiophosphonyl radical cyclisation to form an N-heterocycle, see: Gautier A., Garipova G., Dubert O., Oulyadi H., Piettre S.R. Tetrahedron Lett. 42:2001;5673-5676.
42. Herpin T.F., Motherwell W.B., Roberts B.P., Roland S., Weibel J.-M. Tetrahedron. 53:1997;15085-15100.
43. Gulea-Purcarescu M., About-Jaudét E., Collignon N. Tetrahedron Lett. 36:1995;6635-6638.