Michael addition-elimination mechanism for nucleophilic substitution reaction of cycloalkenyl iodonium salts and selectivity of 1,2-hydrogen shift in cycloalkylidene intermediate

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 480-488

  Fujita, Morifumi ^a   Wan, Hyeok Kim ^a   Fujiwara, Koji ^a   Okuyama, Tadashi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; HYDROGEN; PROBABILITY DENSITY FUNCTION; SALTS;

ALLYLIC PRODUCT; MICHAEL REACTION; NUCLEOPHILIC SUBSTITUTION REACTIONS;

AROMATIC HYDROCARBONS;

ACETIC ACID; ALKENYL GROUP; ALLYL COMPOUND; CARBENE; CHLOROFORM; CYANIDE; CYCLOHEXENE DERIVATIVE; DIPHENYLIODONIUM SALT; HYDROGEN; LIGAND; VINYL DERIVATIVE;

ARTICLE; ELIMINATION REACTION; MICHAEL ADDITION; SUBSTITUTION REACTION;

EID: 12344292278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049218k     Document Type: Article

References (108)

1. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
2. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
3. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
4. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
5. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
6. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
7. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
8. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
9. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
10. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
11. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
12. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
13. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
14. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
15. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
16. For reviews, see: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447. (b) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274-285. (c) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992. (d) Koser, G. F. In The Chemistry of Functional Groups Supplement D2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1995; Chapter 21. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178. (f) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (g) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 327. (h) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271-1287. (i) Okuyama, T. Rev. Heteroatom Chem. 1999, 21, 257-275. (j) Ochiai, M. J. Organomet. Chem. 2000, 611, 494-508. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584. (l) Okuyama, T. Acc. Chem. Res. 2002, 35, 12-18. (m) Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1-56. (n) Okuyama, T.; Fujita, M. Proc. Jpn. Acad. 2002, 78 (B), 167-172. (o) Stang, P. J. J. Org. Chem. 2003, 68, 2997-3008. (p) Hypervalent Iodine Chemistry. Topics of Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
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41. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
42. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
43. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
44. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
45. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
46. For ligand exchange with metal complex, see: (a) Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 44, 4095-4112. (b) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6317. (c) Moriarty, R M.; Epa, W. R. Tetrahedron Lett. 1992, 33, 4095-4098. (d) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627. (e) Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165. (f) Rang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Org. Chem. 1996, 61, 4720-4724. (g) Hinkle, R. J.; Leri, A. C.; David, G. A.; Erwin, W. M. Org. Lett. 2000, 2, 1521-1523.
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56. For theoretical studies on the hydrogen shift in carbenes, see: (a) Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 9148-9156. (b) Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 10426-10427. (c) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682-5689. (d) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809.
57. For theoretical studies on the hydrogen shift in carbenes, see: (a) Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 9148-9156. (b) Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 10426-10427. (c) Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682-5689. (d) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805-10809.
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60. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
61. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
62. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
63. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
64. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
65. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
66. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
67. For Michael additions to vinyl onium salts, see the following. (a) Phosphonium salts: McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202-206. Minami, T.; Sako, H.; Ikehira, T.; Hanamoto, T.; Hirao, I. J. Org. Chem. 1983, 48, 2569-2572. Just, G.; O'Connor, B. Tetrahedron Lett. 1985, 26, 1799-1802. Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424-1426. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985-9994. (b) Arsonium salts: Manske, R.; Gosselck, J. Tetrahedron 1975, 31, 2121-2124. Nesmeyanov, N. A.; Nikul'shina, V. V.; Kharitonov, V. G.; Petrovskii, P. V.; Reutov, O. A. Izv. Akad. Nauk USSR 1988, 908-910. (c) Selenonium salts: Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042-2047. (d) Sulfonium salts: Knipe, A. C. In The Chemistry of the Sulphonium Group, Part 1; Stirling, C. J. M., Ed.; John Wiley & Sons: Chichester, 1981; Chapter 12.
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89. 15
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