1,1-divinylallene

Angewandte Chemie - International Edition

Volumn 50, Issue 44, 2011, Pages 10425-10428

  Cergol, Katie M ^a   Newton, Christopher G ^a   Lawrence, Andrew L ^a   Willis, Anthony C ^a   Paddon Row, Michael N ^b   Sherburn, Michael S ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

1,1 divinylallene; cycloaddition; Diels Alder reactions; hydrocarbons

Indexed keywords

1,1-DIVINYLALLENE; C-C BONDS; DIELS-ALDER CYCLOADDITIONS; DIELS-ALDER REACTIONS; ONE STEP; RING SYSTEMS; SMALL MOLECULES;

OLEFINS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

EID: 80055012811     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105541     Document Type: Article

References (49)

1. H. Hopf, in Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, Wiley-VCH, Weinheim, 2000.
2. S. Fielder, D. D. Rowan, M. S. Sherburn, Angew. Chem. 2000, 112, 4501-4503
3. Angew. Chem. Int. Ed. 2000, 39, 4331-4333.
4. A. D. Payne, G. Bojase, M. N. Paddon-Row, M. S. Sherburn, Angew. Chem. 2009, 121, 4930-4933
5. Angew. Chem. Int. Ed. 2009, 48, 4836-4839.
6. A. D. Payne, A. C. Willis, M. S. Sherburn, J. Am. Chem. Soc. 2005, 127, 12188-12189.
7. G. Bojase, A. D. Payne, A. C. Willis, M. S. Sherburn, Angew. Chem. 2008, 120, 924-926
8. Angew. Chem. Int. Ed. 2008, 47, 910-912.
9. R. Kuhn, H. Fischer, D. Rewicki, H. Fischer, Justus Liebigs Ann. Chem. 1965, 689, 1-20.
10. H. Fischer, H. Fischer, Chem. Ber. 1966, 99, 658-669.
11. H. Fischer, H. Fischer, Chem. Ber. 1967, 100, 755-766.
12. C. K. Tseng, K. G. Migliorese, S. I. Miller, Tetrahedron 1974, 30, 377-383.
13. F. Lehrich, H. Hopf, Tetrahedron Lett. 1987, 28, 2697-2700.
14. F. Lehrich, H. Hopf, J. Grunenberg, Eur. J. Org. Chem. 2011, 2705-2718.
15. See, for example: R. Hayashi, R. P. Hsung, J. B. Feltenberger, A. G. Lohse, Org. Lett. 2009, 11, 2125-2128
16. R. Hayashi, J. B. Feltenberger, R. P. Hsung, Org. Lett. 2010, 12, 1152-1155
17. R. Hayashi, J. B. Feltenberger, A. G. Lohse, M. C. Walton, R. P. Hsung, Beilstein J. Org. Chem. 2011, 7, 410-420.
18. L. A. Curtiss, P. C. Redfern, K. Raghavachari, J. Chem. Phys. 2007, 126, 084108.
19. T. A. Bradford, A. D. Payne, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, J. Org. Chem. 2010, 75, 491-494.
20. K. Ruitenberg, H. Kleijn, C. J. Elsevier, J. Meijer, P. Vermeer, Tetrahedron Lett. 1981, 22, 1451-1452
21. E. Keinan, E. Bosch, J. Org. Chem. 1986, 51, 4006-4016
22. T. Mandai, M. Ogawa, H. Yamaoki, T. Nakata, H. Murayama, M. Kawada, J. Tsuji, Tetrahedron Lett. 1991, 32, 3397-3398
23. T. Moriya, N. Miyaura, A. Suzuki, Synlett 1994, 149-151
24. S. Ma, A. Zhang, J. Org. Chem. 2002, 67, 2287-2294
25. S. Ma, G. Wang, Angew. Chem. 2003, 115, 4347-4349
26. Angew. Chem. Int. Ed. 2003, 42, 4215-4217
27. K. S. Feldman, M. R. Iyer, J. Am. Chem. Soc. 2005, 127, 4590-4591
28. R. Riveiros, D. Rodríguez, J. Pérez Sestelo, L. A. Sarandeses, Org. Lett. 2006, 8, 1403-1406
29. G. A. Molander, E. M. Sommers, S. R. Baker, J. Org. Chem. 2006, 71, 1563-1568
30. P. H. Lee, K. Lee, Y. Kang, J. Am. Chem. Soc. 2006, 128, 1139-1146
31. D. R. Williams, A. A. Shah, Chem. Commun. 2010, 46, 4297-4299.
32. R. Baudouy, J. Gore, J. Chem. Res. Synop. 1981, 278-279
33. S. A. Vorskanyan, Zh. A. Fobanyan, Sh. O. Badanyan, Arm. Khim. Zh. 1987, 40, 181-188.
34. K. B. Sharpless, M. W. Young, J. Org. Chem. 1975, 40, 947-949
35. P. A. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 1976, 41, 1485-1486.
36. T. A. Bradford, A. D. Payne, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, Org. Lett. 2007, 9, 4861-4864.
37. For related reactions involving the chloroprene Grignard reagent, see:, S. Nunomoto, Y. Yamashita, J. Org. Chem. 1979, 44, 4788-4791.
38. See the Supporting Information for full details.: H. Plieninger, W. Maier-Borst, Angew. Chem. 1963, 75, 1177
39. Angew. Chem. Int. Ed. Engl. 1964, 3, 62.
40. Professor J. Grunenberg has confirmed our findings. J. Grunenberg, personal communication.
41. The term "diene-transmissive" was coined by Tsuge in:, S. Kanemasa, H. Sakoh, E. Wada, O. Tsuge, Bull. Chem. Soc. Jpn. 1985, 58, 3312-3319.
42. For a review of sequences of Diels-Alder reactions, see:, J. D. Winkler, Chem. Rev. 1996, 96, 167-176.
43. Similar cyclic [3]dendralenes are available through cycloisomerizations of allene-ynes and related systems. For representative papers, see: K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187
44. T. Shibata, Y. Takesue, S. Kadowaki, K. Takagi, Synlett 2003, 268-270
45. N. Cadran, K. Cariou, G. Hervé, C. Aubert, L. Fensterbank, M. Malacria, J. Marco-Contelles, J. Am. Chem. Soc. 2004, 126, 3408-3409
46. C. Mukai, F. Inagaki, T. Yoshida, S. Kitagaki, Tetrahedron Lett. 2004, 45, 4117-4121
47. X. Jiang, S. Ma, J. Am. Chem. Soc. 2007, 129, 11600-11607
48. P. H.-Y. Cheong, P. Morganelli, M. R. Luzung, K. N. Houk, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 4517-4526.
49. M06-2X/6-311++G(2df,p)//B3LYP/6-31G(d) value.