A convenient synthesis of new 1-alkynyl-1H-benzotriazoles by reaction of alkynyl(phenyl)iodonium salts with benzotriazole ion

Heterocycles

Volumn 52, Issue 1, 2000, Pages 303-312

  Kitamura, Tsugio ^a   Tashi, Norihiko ^a   Tsuda, Kuniyuki ^a   Chen, Haiying ^a   Fujiwara, Yuzo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; DIPHENYLIODONIUM SALT;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0033978034     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-S25     Document Type: Article

References (44)

1. Recent reviews, see: W.-Q. Fan and A. R. Katritzky, 'Comprehensive Heterocyclic Chemistry II,' Vol 4, ed. by A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Elsevier Science Ltd., Oxford, 1996, pp. 2-126; A. R. Katritzky, X. Lan, and W.-Q. Fan, Synthesis, 1994, 445; A. R. Katritzky and X. Lan, Chem. Soc. Rev., 1994, 363.
2. Recent reviews, see: W.-Q. Fan and A. R. Katritzky, 'Comprehensive Heterocyclic Chemistry II,' Vol 4, ed. by A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Elsevier Science Ltd., Oxford, 1996, pp. 2-126; A. R. Katritzky, X. Lan, and W.-Q. Fan, Synthesis, 1994, 445; A. R. Katritzky and X. Lan, Chem. Soc. Rev., 1994, 363.
3. Recent reviews, see: W.-Q. Fan and A. R. Katritzky, 'Comprehensive Heterocyclic Chemistry II,' Vol 4, ed. by A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Elsevier Science Ltd., Oxford, 1996, pp. 2-126; A. R. Katritzky, X. Lan, and W.-Q. Fan, Synthesis, 1994, 445; A. R. Katritzky and X. Lan, Chem. Soc. Rev., 1994, 363.
4. P. J. Stang and F. Diederich, 'Modern Acetylene Chemistry,' VCH, Weinheim, 1995.
5. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
6. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
7. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
8. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
9. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
10. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
11. A. R. Katritzky, J. Li, and N. Malhotra, Liebigs Ann. Chem., 1992, 843; C. W. Rees and R. C. Storr, J. Chem. Soc. (C), 1969, 1478; M. Märky, H. Schmid, and H-J. Hansen, Helv. Chim. Acta, 1979, 62, 2129; S. J. Barker and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1990, 485; P. A. Wender and C. B. Cooper, Tetrahedron, 1986, 42, 2985; A. R. Katritzky, S. Rachwal, K. C. Caster, F. Mahni, K. W. Law, and O. Rubio, J. Chem. Soc., Perkin Trans. 1, 1987, 781; A. R. Katritzky, R. J. Offerman, P. Cabildo, and M. Soleiman, Recl. Trav. Chim. Pays-Bos, 1988, 107, 641.
12. G. Angelini, M. Hanack, J. Vermehren, and M. Speranza, J. Am. Chem. Soc., 1988, 110, 1298.
13. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
14. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
15. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
16. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
17. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
18. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
19. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
20. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
21. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
22. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
23. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
24. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
25. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
26. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
27. For recent reviews and books, see: G. F. Koser, 'The Chemistry of Functional Groups, Supplement D,' Chapters 18 and 25, ed. by S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1983; A. Varvoglis, Synthesis, 1984, 709; R. M. Moriarty and O. Prakash, Acc. Chem. Res., 1986, 19, 244; E. B. Merkushev, Russ. Chem. Rev. (Eng. Transl.), 1987, 56, 826 (Chem. Abstr., 1988,108, 204265y); R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; A. Varvoglis, 'The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, New York, 1992; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221; T. Kitamura, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1995, 53, 893; P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; H. Togo, Y. Hoshina, G. Nogami, and M. Yokoyama, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1997, 55, 90; A. Varvoglis, 'Hypervalent Iodine in Organic Synthesis,' Academic Press, San Diego, 1997; T. Kitamura and Y. Fujiwara, Org. Prep. Proced.Int.,1997, 29, 409.
28. M. Ochiai and Y. Nagao, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1986, 44, 660; M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92; P. J. Stang, Angew. Chem. Int. Ed Engl., 1992, 31, 274; P. J. Stang, 'Supplement C: The Chemistry of Triple-bonded Functional Groups,' Chapter 20, ed. by S. Patai, John Wiley & Sons, Chichester, 1994; P. J. Stang, ref. 2, Chapter 3.
29. M. Ochiai and Y. Nagao, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1986, 44, 660; M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92; P. J. Stang, Angew. Chem. Int. Ed Engl., 1992, 31, 274; P. J. Stang, 'Supplement C: The Chemistry of Triple-bonded Functional Groups,' Chapter 20, ed. by S. Patai, John Wiley & Sons, Chichester, 1994; P. J. Stang, ref. 2, Chapter 3.
30. M. Ochiai and Y. Nagao, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1986, 44, 660; M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92; P. J. Stang, Angew. Chem. Int. Ed Engl., 1992, 31, 274; P. J. Stang, 'Supplement C: The Chemistry of Triple-bonded Functional Groups,' Chapter 20, ed. by S. Patai, John Wiley & Sons, Chichester, 1994; P. J. Stang, ref. 2, Chapter 3.
31. M. Ochiai and Y. Nagao, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1986, 44, 660; M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92; P. J. Stang, Angew. Chem. Int. Ed Engl., 1992, 31, 274; P. J. Stang, 'Supplement C: The Chemistry of Triple-bonded Functional Groups,' Chapter 20, ed. by S. Patai, John Wiley & Sons, Chichester, 1994; P. J. Stang, ref. 2, Chapter 3.
32. M. Ochiai and Y. Nagao, Yuki Gosei Kagaku Kyokai Shi (J. Synth. Org. Chem. Jpn.), 1986, 44, 660; M. Ochiai, Rev. Heteroatom Chem., 1989, 2, 92; P. J. Stang, Angew. Chem. Int. Ed Engl., 1992, 31, 274; P. J. Stang, 'Supplement C: The Chemistry of Triple-bonded Functional Groups,' Chapter 20, ed. by S. Patai, John Wiley & Sons, Chichester, 1994; P. J. Stang, ref. 2, Chapter 3.
33. T. Kitamura, N. Tashi, K. Tsuda, and Y. Fujiwara, Tetrahedron Lett., 1998, 39, 3787.
34. G. F. Koser, L. Rebrovic, and R. H. Wettach, J. Org. Chem., 1981, 46, 4324; L. Rebrovic and G. F. Koser, J. Org. Chem., 1984, 49, 2462.
35. G. F. Koser, L. Rebrovic, and R. H. Wettach, J. Org. Chem., 1981, 46, 4324; L. Rebrovic and G. F. Koser, J. Org. Chem., 1984, 49, 2462.
36. P. J. Stang and B. W. Surber, J. Am. Chem. Soc., 1985, 107, 1452; P. J. Stang, B. W. Surber, Z.-C. Chen, K. A. Roberts, and A. G. Anderson, J. Am. Chem. Soc., 1987, 109, 228.
37. P. J. Stang and B. W. Surber, J. Am. Chem. Soc., 1985, 107, 1452; P. J. Stang, B. W. Surber, Z.-C. Chen, K. A. Roberts, and A. G. Anderson, J. Am. Chem. Soc., 1987, 109, 228.
38. T. Kitamura and P. J. Stang, J. Org. Chem., 1988, 53, 4105.
39. T. Kitamura, T. Fukuoka, L. Zheng, T. Fujimoto, H. Taniguchi, and Y. Fujiwara, Bull. Chem. Soc. Jpn., 1996, 69, 2649.
40. P. J. Stang, Chem. Rev., 1978, 78, 383; M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro, and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281.
41. P. J. Stang, Chem. Rev., 1978, 78, 383; M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro, and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281.
42. W. M. Jones, 'Rearrangements in Ground and Excited States,' Essay 3, ed. by P. de Mayo, Academic Press, 1980.
43. T. Kitamura and P. J. Stang, Tetrahedron Lett., 1988, 29, 1887.
44. A. R. Katritzky, K. Yannakopoulou, W. Kuzmierkiewicz, J. M. Aurrecoechea, G. J. Palenik, A. E. Koziol, M. Szczeniak, and R. Skarjune, J. Chem. Soc., Perkin Trans. 1, 1987, 2673.