Cycloaddition reactions of iodonium ylides of cyclic β-diketones with 1,3-dienes: Evidence for a stepwise mechanism

Synlett

Volumn , Issue 12, 1999, Pages 1925-1926

  Alexiou, Ioannis ^a   Gogonas, Efstathios P ^a   Hadjiarapoglou, Lazaros P ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

Author keywords

1,3 cycloaddition; 1,3 diene; Dihydrofuran; Hypervalent iodine; Ylide

Indexed keywords

ALKADIENE; DIKETONE;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; IRRADIATION; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0032714672     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2970     Document Type: Article

References (19)

1. Koser, G. F. In The Chemistry of Functional Groups, Supplement D; Wiley: New York 1983; Chapter 18. Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York 1992. Varvoglis, A Hypervalent Iodine in Organic Synthesis; Academic Press: London 1997.
2. Koser, G. F. In The Chemistry of Functional Groups, Supplement D; Wiley: New York 1983; Chapter 18. Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York 1992. Varvoglis, A Hypervalent Iodine in Organic Synthesis; Academic Press: London 1997.
3. Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York 1992. Varvoglis, A Hypervalent Iodine in Organic Synthesis; Academic Press: London 1997.
4. For a general synthesis of β-dicarbonyl iodonium ylides, see: Schank, K.; Lick, C. Synthesis 1983, 393-395.
5. For a general synthesis of β-disulfonyl iodonium ylides, see: Hadjiarapoglou, L.; Varvoglis, A.; Alcock, N.W.; Pike, G.A. J. Chem. Soc., Perkin Trans 1 1988, 2839-2846.
6. Moriarty, R.M.; Kim, J.; Guo, L. Tetrahedron Lett. 1993, 34, 4129-4132. Moriarty, R.M.; Prakash, O.; Vaid, R.K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443-6444. Moriarty, R.M.; May, E.J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333-4336. Moriarty, R.M.; May, E.J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765-766.
7. Moriarty, R.M.; Kim, J.; Guo, L. Tetrahedron Lett. 1993, 34, 4129-4132. Moriarty, R.M.; Prakash, O.; Vaid, R.K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443-6444. Moriarty, R.M.; May, E.J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333-4336. Moriarty, R.M.; May, E.J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765-766.
8. Moriarty, R.M.; Kim, J.; Guo, L. Tetrahedron Lett. 1993, 34, 4129-4132. Moriarty, R.M.; Prakash, O.; Vaid, R.K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443-6444. Moriarty, R.M.; May, E.J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333-4336. Moriarty, R.M.; May, E.J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765-766.
9. Moriarty, R.M.; Kim, J.; Guo, L. Tetrahedron Lett. 1993, 34, 4129-4132. Moriarty, R.M.; Prakash, O.; Vaid, R.K.; Zhao, L. J. Am. Chem. Soc. 1989, 111, 6443-6444. Moriarty, R.M.; May, E.J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333-4336. Moriarty, R.M.; May, E.J.; Guo, L.; Prakash, O. Tetrahedron Lett. 1998, 39, 765-766.
10. Mueller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958. Spyroudis, S.; Tarantili, P. J. Org. Chem. 1993, 58, 4885-4889. Wu, C.; Johnson, R.K.; Mattern, M.R.; Wong, J.C.; Kingston, D.G.I. J. Nat. Prod. 1999, 62, 963-968.
11. Mueller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958. Spyroudis, S.; Tarantili, P. J. Org. Chem. 1993, 58, 4885-4889. Wu, C.; Johnson, R.K.; Mattern, M.R.; Wong, J.C.; Kingston, D.G.I. J. Nat. Prod. 1999, 62, 963-968.
12. Mueller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947-958. Spyroudis, S.; Tarantili, P. J. Org. Chem. 1993, 58, 4885-4889. Wu, C.; Johnson, R.K.; Mattern, M.R.; Wong, J.C.; Kingston, D.G.I. J. Nat. Prod. 1999, 62, 963-968.
13. Hadjiarapoglou, L. P. Tetrahedron Lett. 1987, 28, 4449-4450. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron Lett. 1989, 30, 6673-6676. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron 1997, 53, 9365-9376. Asouti, A.; Hadjiarapoglou, L.P. Tetrahedron Lett. 1998, 39, 9073-9076.
14. Hadjiarapoglou, L. P. Tetrahedron Lett. 1987, 28, 4449-4450. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron Lett. 1989, 30, 6673-6676. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron 1997, 53, 9365-9376. Asouti, A.; Hadjiarapoglou, L.P. Tetrahedron Lett. 1998, 39, 9073-9076.
15. Hadjiarapoglou, L. P. Tetrahedron Lett. 1987, 28, 4449-4450. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron Lett. 1989, 30, 6673-6676. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron 1997, 53, 9365-9376. Asouti, A.; Hadjiarapoglou, L.P. Tetrahedron Lett. 1998, 39, 9073-9076.
16. Hadjiarapoglou, L. P. Tetrahedron Lett. 1987, 28, 4449-4450. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron Lett. 1989, 30, 6673-6676. Hadjiarapoglou, L. P.; Schank, K. Tetrahedron 1997, 53, 9365-9376. Asouti, A.; Hadjiarapoglou, L.P. Tetrahedron Lett. 1998, 39, 9073-9076.
17. 2/AcOEt) afforded dihydrofuran 3.
18. 3, 100 MHz) : δ = 21.6, 24.0, 26.3, 36.3, 37.8, 91.0, 112.3, 113.1, 140.6, 176.0, 195.6.
19. The postulation of such intermediates was based on the observation that various alkenes and alkynes reacted with a β-disulfonyl iodonium ylide in the absence of light, see: Hadjiarapoglou, L.P. Ph.D Thesis, University of Thessaloniki, Gogonas, E.P.; Hadjiarapoglou, L.P. unpublished results. No reaction was observed, when the β-dicarbonyl iodonium ylide 1 was used instead.