Nucleophilic Vinylic Substitutions of (Z)-(β-Haloalkenyl)phenyliodonium Salts with Sodium Benzenesulfinate: First Evidence of a Michael Addition of Nucleophiles to Alkenyliodonium Salts at the Cβ Atom

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8001-8008

  Ochiai, Masahito ^a   Kitagawa, Yutaka ^a   Toyonari, Mika ^a   Uemura, Koji ^b   Oshima, Kunio ^b   Shiro, Motoo ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^c RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000958698     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970735v     Document Type: Article

References (76)

1. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
2. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
3. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
4. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
5. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
6. For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
7. (a) Enolate anions: Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23. Kitamura, T.; Nagata, K.; Taniguchi, H. Tetrahedron Lett. 1995, 36, 1081.
8. (a) Enolate anions: Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23. Kitamura, T.; Nagata, K.; Taniguchi, H. Tetrahedron Lett. 1995, 36, 1081.
9. (a) Enolate anions: Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23. Kitamura, T.; Nagata, K.; Taniguchi, H. Tetrahedron Lett. 1995, 36, 1081.
10. (a) Enolate anions: Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23. Kitamura, T.; Nagata, K.; Taniguchi, H. Tetrahedron Lett. 1995, 36, 1081.
11. (a) Enolate anions: Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23. Kitamura, T.; Nagata, K.; Taniguchi, H. Tetrahedron Lett. 1995, 36, 1081.
12. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
13. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
14. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
15. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
16. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
17. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
18. (b) Oxygen nucleophiles: Stang, P. J.; Surber, B. W. J. Am. Chem. Soc. 1985, 107, 1452. Stang, P. J.; Boehshar, M.; Lin, J. J. Am. Chem. Soc. 1986, 108, 7832. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272. Stang, P. J.; Kitamura, T.; Boehshar, M.; Wingert, H. J. Am. Chem. Soc. 1989, 111, 2225. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1989, 54, 4038. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055. Shu, T.; Chen, D.-W.; Ochiai, M. Tetrahedron Lett. 1996, 37, 5539.
19. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
20. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
21. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
22. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
23. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
24. Nitrogen nucleophiles: Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255, 50. Kunz, R.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 330. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722. Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
25. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
26. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
27. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
28. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
29. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
30. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
31. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
32. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
33. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
34. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
35. Sulfur nucleophiles: Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1990, 112, 6437. Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1991, 113, 4571. Kitamura, T.; Furuki, R.; Zheng, L.; Fujimoto, T.; Taniguchi, H. Chem. Lett. 1992, 2241. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1995, 68, 3637. Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535. Williamson, B. L.; Murch, P.; Fischer, D. R.; Stang, P. J. Synlett 1993, 858. Tykwinski, R. R.; Williamson, B. L.; Fischer, D. R.; Stang, P. J.; Arif, A. M. J. Org. Chem. 1993, 58, 5235. Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. Liu, Z.-D.; Chen, Z.-C. Synth. Commun. 1992, 22, 1997. Liu, Z.-D.; Chen, Z.-C. J. Org. Chem. 1993, 58, 1924.
36. (e) Phosphites: Lodaya, J. S.; Koser, G. F. J. Org. Chem. 1990, 55, 1513.
37. Okuyama, T.; Takino, T.; Sueda, T.; Ochiai, M. J. Am. Chem. Soc. 1995, 117, 3360.
38. (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095.
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44. Ochiai, M.; Oshima, K.; Masaki, Y. Chem. Lett. 1994, 871.
45. Zefirov, N. S.; Kozmin, A. S.; Kasumov, T.; Potekhin, K. A.; Sorokin, V. D.; Brel, V. K.; Abramkin, E. V.; Struchkov, Y. T.; Zhdankin, V. V.; Stang, P. J. J. Org. Chem. 1992, 57, 2433.
46. A part of this work has been reported in a preliminary form: Ochiai, M.; Kitagawa, K.; Toyonari, M.; Uemura, K. Tetrahedron Lett. 1994, 35, 9407.
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48. For synthesis of alkynyl(phenyl)iodonium tetrafluoroborates 1, see: (a) Ochiai, M.; Kunishima, M.; Sumi, K.; Nagao, Y.; Fujita, E. Tetrahedron Lett. 1985, 26, 4501. (b) Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Fujita, E. J. Chem. Soc., Chem. Commun. 1987, 1708.
49. Ochiai, M.; Uemura, K.; Oshima, K.; Masaki, Y.; Kunishima, M.; Tani, S. Tetrahedron Lett. 1991, 32, 4753.
50. Ochiai, M.; Oshima, K.; Masaki, Y. Chem. Lett. 1994, 871.
51. Hinkle, R. J.; Stang, P. J. Synthesis 1994, 313.
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61. 14a
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63. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
64. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
65. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
66. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
67. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
68. For reviews of nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1. (b) Modena, G. Acc. Chem. Res. 1971, 4, 73. (c) Miller, S. I. Tetrahedron 1977, 33, 1211. (d) Rappoport, Z. Acc. Chem. Res. 1981, 14, 7. (e) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309. (f) Shainyan, B. A. Usp. Khim. 1986, 55, 942. (g) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
69. Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1979, 101, 5095.
70. (a) Oae, S.; Uchida, Y. Acc. Chem. Res. 1991, 24, 202.
71. (b) Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341.
72. Ochiai, M.; Uemura, K.; Masaki, Y. J. Am. Chem. Soc. 1993, 115, 2528.
73. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
74. (a) Marchese, G.; Modena, G.; Naso, F. Tetrahedron 1968, 24, 663.
75. (b) Marchese, G.; Modena, G.; Naso, F. J. Chem. Soc. (B) 1969, 290.
76. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.