Aromatic C-H insertion of β-phenoxyalkylidenecarbenes generated by reaction of alkynyl(p-phenylene)bisiodonium ditrifluoro-methanesulfonates (ditriflates) with phenoxide anions

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 8, 1997, Pages 1511-1515

  Kitamura, Tsugio ^a   Zheng, Lei ^a   Fukuoka, Takahiro ^a   Fujiwara, Yuzo ^a   Taniguchi, Hiroshi ^a   Sakurai, Makoto ^b   Tanaka, Ryuichi ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b FUKUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000377410     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700602k     Document Type: Article

References (59)

1. (a) A. Varvoglis, Chem. Soc. Rev., 1981, 10, 377;
2. (b) T. Umemoto, J. Synth. Org. Chem. Jpn., 1983, 41, 251;
3. (c) G. F. Koser, in The Chemistry of Functional Groups, Supplement D, ed. S. Patai and Z. Rappoport, Wiley, New York, 1983, ch. 18 and 25;
4. (d) A. Varvoglis, Synthesis, 1984, 709;
5. (e) R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244;
6. (f) M. Ochiai and Y. Nagao, J. Synth. Org. Chem. Jpn., 1986, 44, 660;
7. (g) E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826;
8. (h) M. Ochiai, Rev. Heteroatom. Chem., 1989, 2, 92;
9. R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431;
10. (j) R. M. Moriarty, R. K. Vaid and G. F. Koser, Synlett, 1990, 365;
11. (k) P. J. Stang, Angew. Chem., Int. Ed Engl., 1992, 31, 274;
12. A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, New York, 1992;
13. Y. Kita, H. Tohma and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113;
14. (n) Y. Kita and H. Tohma, Farumashia, 1992, 28, 984;
15. (o) O. Prakash and S. P. Singh, Aldrichim. Acta, 1994, 27, 15;
16. (p) G. F. Koser, in The Chemistry of Functional Groups, Supplement D2, ed. S. Patai and Z. Rappoport, Wiley, New York, 1995, ch. 21;
17. (q) T. Kitamura, J. Synth. Org. Chem. Jpn., 1995, 53, 893;
18. (r) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123.
19. (a) F. M. Beringer and S. A. Galton, J. Org. Chem., 1965, 30, 1930;
20. (b) P. J. Stang, M. Boeshar and J. Lin, J. Am. Chem. Soc., 1986, 108, 7832;
21. (c) P. J. Stang, T. Kitamura, M. Boeshar and H. Wingert, J. Am. Chem. Soc., 1989, 111, 2225;
22. (d) M. Ochiai, T. Itao, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani and Y. Nagao, J. Chem. Soc., Chem. Commun., 1990, 118;
23. (e) J. S. Lodaya and G. F. Koser, J. Org. Chem., 1990, 55, 1513;
24. (f) M. Bachi, N. Bar-Ner, C. M. Crittell, P. J. Stang and B. L. Williamson, J. Org. Chem., 1991, 56, 3912;
25. (g) D. R. Fisher, B. L. Williamson and P. J. Stang, Synlett, 1992, 535;
26. (h) P. J. Stang and C. M. Crittell, J. Org. Chem., 1992, 57, 4306.
27. (a) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281;
28. (b) M. Ochiai, Y. Takaoka and Y. Nagao, J. Am. Chem. Soc., 1988, 110, 6565;
29. (c) T. Kitamura and P. J. Stang, Tetrahedron Lett.. 1988, 29, 1887;
30. (d) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3134.
31. T. Kitamura, L. Zheng, H. Taniguchi, M. Sakurai and K. Tanaka, Tetrahedron Lett., 1993, 34, 4055.
32. 4 a few examples of aromatic C-H insertion in solution have been reported. (a) R. R. Tykwinski, J. A. Whiteford and P. J. Stang, J. Chem. Soc., Chem. Commun., 1993, 1800; (b) M. Ochiai, unpublished results, see ref 1(p), p. 1274; (c) K. S. Feldman, M. M. Bruendl and K. Schildknegt, J. Org. Chem., 1995, 60, 7722. Aromatic C-H insertion of alkylidenecarbenes in solution has not been reviewed, see ref. 7. Aromatic C-H insertions of alkyli- denecarbenes have been observed only in the gas phase. For a review on the reactions in the gas phase, see R. R. C. Brown and F. W. Eastwood, Synlett, 1993, 9.
33. 4 a few examples of aromatic C-H insertion in solution have been reported. (a) R. R. Tykwinski, J. A. Whiteford and P. J. Stang, J. Chem. Soc., Chem. Commun., 1993, 1800; (b) M. Ochiai, unpublished results, see ref 1(p), p. 1274; (c) K. S. Feldman, M. M. Bruendl and K. Schildknegt, J. Org. Chem., 1995, 60, 7722. Aromatic C-H insertion of alkylidenecarbenes in solution has not been reviewed, see ref. 7. Aromatic C-H insertions of alkyli- denecarbenes have been observed only in the gas phase. For a review on the reactions in the gas phase, see R. R. C. Brown and F. W. Eastwood, Synlett, 1993, 9.
34. 4 a few examples of aromatic C-H insertion in solution have been reported. (a) R. R. Tykwinski, J. A. Whiteford and P. J. Stang, J. Chem. Soc., Chem. Commun., 1993, 1800; (b) M. Ochiai, unpublished results, see ref 1(p), p. 1274; (c) K. S. Feldman, M. M. Bruendl and K. Schildknegt, J. Org. Chem., 1995, 60, 7722. Aromatic C-H insertion of alkylidenecarbenes in solution has not been reviewed, see ref. 7. Aromatic C-H insertions of alkyli- denecarbenes have been observed only in the gas phase. For a review on the reactions in the gas phase, see R. R. C. Brown and F. W. Eastwood, Synlett, 1993, 9.
35. 4 a few examples of aromatic C-H insertion in solution have been reported. (a) R. R. Tykwinski, J. A. Whiteford and P. J. Stang, J. Chem. Soc., Chem. Commun., 1993, 1800; (b) M. Ochiai, unpublished results, see ref 1(p), p. 1274; (c) K. S. Feldman, M. M. Bruendl and K. Schildknegt, J. Org. Chem., 1995, 60, 7722. Aromatic C-H insertion of alkylidenecarbenes in solution has not been reviewed, see ref. 7. Aromatic C-H insertions of alkyli-denecarbenes have been observed only in the gas phase. For a review on the reactions in the gas phase, see R. R. C. Brown and F. W. Eastwood, Synlett, 1993, 9.
36. T. Kitamura, R. Furuki, L. Zheng, T. Fujimoto and H. Taniguchi, Chem. Lett., 1992, 2241. The pure product (>95%) is obtained only by extraction with diethyl ether. In some cases, chromatography is also required for purification.
37. (a) W. Kirmse, Carbene Chemistry, Academic Press, New York, 1971;
38. (b) M. Jones and R. A. Moss, Carbenes, Wiley-Interscience, New York, 1973;
39. (c) P. J. Stang, Chem. Rev., 1978, 78, 383;
40. (d) P. J. Stang Acc. Chem. Res., 1982, 15, 348;
41. (e) A. Oku and T. Harada, J. Synth. Org. Chem. Jpn., 1986, 44, 736;
42. (f) A. Oku, J. Synth. Org. Chem. Jpn., 1990, 48, 710.
43. T. Kitamura, J. Matsuyuki and H. Taniguchi, Synthesis, 1994, 147; T. Kitamura, J. Matsuyuki, K. Nagata, R. Furuki and H. Taniguchi, Synthesis, 1992, 945.
44. T. Kitamura, J. Matsuyuki and H. Taniguchi, Synthesis, 1994, 147; T. Kitamura, J. Matsuyuki, K. Nagata, R. Furuki and H. Taniguchi, Synthesis, 1992, 945.
45. P. J. Stang and M. G. Mangum, J. Am. Chem. Soc., 1975, 97 6478; M. Ochiai, T. Sueda, K. Uemura and Y. Masaki, J. Org. Chem., 1995, 60, 2624.
46. P. J. Stang and M. G. Mangum, J. Am. Chem. Soc., 1975, 97 6478; M. Ochiai, T. Sueda, K. Uemura and Y. Masaki, J. Org. Chem., 1995, 60, 2624.
47. P. J. Stang, M. Boeshar, H. Wingert and T. Kitamura, J. Am. Chem. Soc., 1988, 110, 3272.
48. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
49. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
50. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
51. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
52. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
53. M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; M. Ochiai, K. Oshima and Y. Masaki, Tetrahedron Lett., 1991, 32, 7711; M. Ochiai, K. Uemura, K. Oshima, Y. Masaki, M. Kunishima and S. Tani, Tetrahedron Lett., 1991, 32, 4753; M. Ochiai, M. Kunishima, K. Fuji and Y. Nagao, J. Org. Chem., 1988, 53, 6144; T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887; P. J. Stang, H. Wingert and A. M. Arif, J. Am. Chem. Soc., 1987, 109, 7235.
54. H. Saltzman and J. G. Sharefkin, Org. Synth., 1973, Coll. Vol. 5, 658.
55. T. Kitamura, R. Furuki, L. Zheng, K. Nagata, T. Fukuoka, Y. Fujiwara and H. Taniguchi, Bull. Chem. Soc. Jpn., 1995, 68, 3637; T. Kitamura, R. Furuki, L. Zheng, T. Fujimoto and H. Taniguchi, Chem. Lett., 1992, 2241.
56. T. Kitamura, R. Furuki, L. Zheng, K. Nagata, T. Fukuoka, Y. Fujiwara and H. Taniguchi, Bull. Chem. Soc. Jpn., 1995, 68, 3637; T. Kitamura, R. Furuki, L. Zheng, T. Fujimoto and H. Taniguchi, Chem. Lett., 1992, 2241.
57. A. Hercouet and M. LeCorre, Tetrahedron, 1981, 37, 2867.
58. R. Beuqelmans and H. Ginsburg, J. Chem. Soc., Chem. Commun., 1980, 508.
59. D. R. Buckle and C. J. M. Rockell, J. Chem. Soc., Perkin Trans. 1, 1985, 2443.