The conversion of furan-, thiophene- and selenophene-2-carbonyl azidesintoisocyanates: A DSC analysis

Arkivoc

Volumn 2002, Issue 11, 2002, Pages 6-16

  Salatelli, Elisabetta ^a   Zanirato, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Curtius rearrangement; Differential scanning calorimetry; Heteroaroyl azides

Indexed keywords

2 ISOCYANATOSELENOPHENE; 2 THIENYLISOCYANATE; 5 (TRIMETHYLSILYL) 2 THIENYLISOCYANATE; 5 (TRIMETHYLSILYL)THIOPHENE 2 CARBONYL AZIDE; 5 METHYL 2 THIENYLISOCYANATE; 5 METHYLTHIOPHENE 2 CARBONYL AZIDE; AZIDE; CARBONYL DERIVATIVE; FURAN 2 CARBONYL AZIDE; FURAN DERIVATIVE; ISOCYANIC ACID DERIVATIVE; SELENOPHENE 2 CARBONYL AZIDE; THIOPHENE 2 CARBONYL AZIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CURTIUS REARRANGEMENT; DIFFERENTIAL SCANNING CALORIMETRY;

EID: 3242780810     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (68)

1. Advertising campaign of Aldrich Chemicals, Milwaukee, U.S.A.
2. R. Richter and H. Ulrich, The Chemistry of Cyanates and their Thioderivatives, S. Patai ed., Wiley, Chichester, 1977, 619; H. Ulrich, Chemistry and Technology of Isocyanates, Wiley, Chichester, 1996; M. Bierwisch, W. Abraham, J. Inf. Rec., 1998, 24, 329.
3. R. Richter and H. Ulrich, The Chemistry of Cyanates and their Thioderivatives, S. Patai ed., Wiley, Chichester, 1977, 619; H. Ulrich, Chemistry and Technology of Isocyanates, Wiley, Chichester, 1996; M. Bierwisch, W. Abraham, J. Inf. Rec., 1998, 24, 329.
4. R. Richter and H. Ulrich, The Chemistry of Cyanates and their Thioderivatives, S. Patai ed., Wiley, Chichester, 1977, 619; H. Ulrich, Chemistry and Technology of Isocyanates, Wiley, Chichester, 1996; M. Bierwisch, W. Abraham, J. Inf. Rec., 1998, 24, 329.
5. th ed., 2001, 1410; D. V. Banthorpe, The Chemistry of the Azido Group, S. Patai, ed., Wiley, New York, 1971, 397.
6. M. B. Smith and J. March, Advanced Organic Chemistry, Wiley, New York, 5(th) ed., 2001, 1410; D. V. Banthorpe, The Chemistry of the Azido Group, S. Patai, ed., Wiley, New York, 1971, 397.
7. P. A. S. Smith, Org. Reactions, 1946, 3, 337; J. H. Saunders and R. J. Slocombe, Chem. Rev., 1948, 43, 205; W. Lwowski, in The Chemistry of the Azido Group, S. Patai, ed., Wiley, London, 1971, 503; T. Shioiri, Comprehensive Organic Synthesis, E. Winterfeldt, ed., Pergamon, Oxford, 1991, 6, 795; P. Molina and A. Tarraga, Comprehensive Organic Functional Group Transformation, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, 5, 961.
8. P. A. S. Smith, Org. Reactions, 1946, 3, 337; J. H. Saunders and R. J. Slocombe, Chem. Rev., 1948, 43, 205; W. Lwowski, in The Chemistry of the Azido Group, S. Patai, ed., Wiley, London, 1971, 503; T. Shioiri, Comprehensive Organic Synthesis, E. Winterfeldt, ed., Pergamon, Oxford, 1991, 6, 795; P. Molina and A. Tarraga, Comprehensive Organic Functional Group Transformation, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, 5, 961.
9. P. A. S. Smith, Org. Reactions, 1946, 3, 337; J. H. Saunders and R. J. Slocombe, Chem. Rev., 1948, 43, 205; W. Lwowski, in The Chemistry of the Azido Group, S. Patai, ed., Wiley, London, 1971, 503; T. Shioiri, Comprehensive Organic Synthesis, E. Winterfeldt, ed., Pergamon, Oxford, 1991, 6, 795; P. Molina and A. Tarraga, Comprehensive Organic Functional Group Transformation, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, 5, 961.
10. P. A. S. Smith, Org. Reactions, 1946, 3, 337; J. H. Saunders and R. J. Slocombe, Chem. Rev., 1948, 43, 205; W. Lwowski, in The Chemistry of the Azido Group, S. Patai, ed., Wiley, London, 1971, 503; T. Shioiri, Comprehensive Organic Synthesis, E. Winterfeldt, ed., Pergamon, Oxford, 1991, 6, 795; P. Molina and A. Tarraga, Comprehensive Organic Functional Group Transformation, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, 5, 961.
11. P. A. S. Smith, Org. Reactions, 1946, 3, 337; J. H. Saunders and R. J. Slocombe, Chem. Rev., 1948, 43, 205; W. Lwowski, in The Chemistry of the Azido Group, S. Patai, ed., Wiley, London, 1971, 503; T. Shioiri, Comprehensive Organic Synthesis, E. Winterfeldt, ed., Pergamon, Oxford, 1991, 6, 795; P. Molina and A. Tarraga, Comprehensive Organic Functional Group Transformation, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, 5, 961.
12. M. Prats and C. Galvez, Heterocycles 1992, 34, 149; M. N. Belgacem, J. Quillerou, A. Gandini, J. Rivero and G. Roux, Eur. Pol. J., 1989, 25, 1125; H. Saikachi, T. Kitagawa, Chem. Pharm. Bull. 1978, 26, 1054 and references therein.
13. M. Prats and C. Galvez, Heterocycles 1992, 34, 149; M. N. Belgacem, J. Quillerou, A. Gandini, J. Rivero and G. Roux, Eur. Pol. J., 1989, 25, 1125; H. Saikachi, T. Kitagawa, Chem. Pharm. Bull. 1978, 26, 1054 and references therein.
14. M. Prats and C. Galvez, Heterocycles 1992, 34, 149; M. N. Belgacem, J. Quillerou, A. Gandini, J. Rivero and G. Roux, Eur. Pol. J., 1989, 25, 1125; H. Saikachi, T. Kitagawa, Chem. Pharm. Bull. 1978, 26, 1054 and references therein.
15. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
16. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
17. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
18. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
19. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
20. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
21. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
22. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
23. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
24. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
25. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
26. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
27. For a variation that conveniently produces the heteroaryl amines (or others) directly see: H. M. Singleton and W. R. Edwards, J. Am. Chem. Soc. 1938, 60, 540; J. Weinstock, J. Org. Chem. 1961, 26, 3511; J. B. Sullivan and W. C. McCarthy, J. Org. Chem., 1965, 30, 662; R. K. Smalley and T. E. Bingham, J. Chem. Soc. (C) 1969, 2481; G. Ha-Kow, C. Paulmier and P. Pastour, Bull. Soc. Chim. Fr., 1976, 151; W. C. McCarthy and L. E. Foss, J. Org. Chem. 1977, 42, 1508; W. Ried and R. Christ, Liebig's Ann. Chem. 1980, 693; B. Stanovnik, M. Tisler, V. Golob, I. Hvala and O. Nicolic, J. Heterocyclic Chem. 1980, 17, 733; J. R. Pfister and W. E. Wyman, Synthesis 1983, 38; T. L. Capson and C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515; T. Shioiri, M. Murata and Y. Hamada, Chem. Pharm. Bull. 1987, 35, 2698; A. Padwa, M. A. Brodney, B. Liu, K. Satake and T. Wu, J. Org. Chem. 1999, 64, 3595; F. Danielli and P. Zanirato, ARKIVOC, 2000, 1, 67.
28. See for example, C. R. Hauser and S. W. Kantor, J. Am. Chem. Soc. 1950, 72, 4284; P. A. S. Smith, Molecular Rearrangements, ed. P. de Mayo, Interscience, New York, 1963, 528; P. A. S. Smith, Open Chain Nitrogen Compounds, Benjamin W. A., New York, 1966, 2, 220. W. Lwowski, Angew. Chem. Int. Ed. Engl. 1967, 1967, 6, 897; S. Linke, G. T. Tissue and W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6308.
29. See for example, C. R. Hauser and S. W. Kantor, J. Am. Chem. Soc. 1950, 72, 4284; P. A. S. Smith, Molecular Rearrangements, ed. P. de Mayo, Interscience, New York, 1963, 528; P. A. S. Smith, Open Chain Nitrogen Compounds, Benjamin W. A., New York, 1966, 2, 220. W. Lwowski, Angew. Chem. Int. Ed. Engl. 1967, 1967, 6, 897; S. Linke, G. T. Tissue and W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6308.
30. See for example, C. R. Hauser and S. W. Kantor, J. Am. Chem. Soc. 1950, 72, 4284; P. A. S. Smith, Molecular Rearrangements, ed. P. de Mayo, Interscience, New York, 1963, 528; P. A. S. Smith, Open Chain Nitrogen Compounds, Benjamin W. A., New York, 1966, 2, 220. W. Lwowski, Angew. Chem. Int. Ed. Engl. 1967, 1967, 6, 897; S. Linke, G. T. Tissue and W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6308.
31. See for example, C. R. Hauser and S. W. Kantor, J. Am. Chem. Soc. 1950, 72, 4284; P. A. S. Smith, Molecular Rearrangements, ed. P. de Mayo, Interscience, New York, 1963, 528; P. A. S. Smith, Open Chain Nitrogen Compounds, Benjamin W. A., New York, 1966, 2, 220. W. Lwowski, Angew. Chem. Int. Ed. Engl. 1967, 1967, 6, 897; S. Linke, G. T. Tissue and W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6308.
32. See for example, C. R. Hauser and S. W. Kantor, J. Am. Chem. Soc. 1950, 72, 4284; P. A. S. Smith, Molecular Rearrangements, ed. P. de Mayo, Interscience, New York, 1963, 528; P. A. S. Smith, Open Chain Nitrogen Compounds, Benjamin W. A., New York, 1966, 2, 220. W. Lwowski, Angew. Chem. Int. Ed. Engl. 1967, 1967, 6, 897; S. Linke, G. T. Tissue and W. Lwowski, J. Am. Chem. Soc. 1967, 89, 6308.
33. J. Stieglitz, Am. Chem. J. 1896, 18, 751.
34. Fry and J. C. Wright, Chem. Eng. News, 28, 1968; R. K. Smalley, T. E. Bingham, J. Chem. Soc. C 1969, 2481; W. Lwowski, R. A. de Muriac and M. Thompson, J. Org. Chem. 1975, 40, 2608.
35. Fry and J. C. Wright, Chem. Eng. News, 28, 1968; R. K. Smalley, T. E. Bingham, J. Chem. Soc. C 1969, 2481; W. Lwowski, R. A. de Muriac and M. Thompson, J. Org. Chem. 1975, 40, 2608.
36. Fry and J. C. Wright, Chem. Eng. News, 28, 1968; R. K. Smalley, T. E. Bingham, J. Chem. Soc. C 1969, 2481; W. Lwowski, R. A. de Muriac and M. Thompson, J. Org. Chem. 1975, 40, 2608.
37. H. Saikachi, T. Kitagawa, A. Nasu, and H. Sasaki, Chem. Pharm. Bull. 1981, 29, 237, and references therein.
38. W. Lwowski, Azides and Nitrenes, E. F. V. Scriven ed., Academic Press, Orlando, 1984, 205; S. Batori, A. Messmer and H.-J. Timpe, Heterocycles 1991, 32, 649.
39. W. Lwowski, Azides and Nitrenes, E. F. V. Scriven ed., Academic Press, Orlando, 1984, 205; S. Batori, A. Messmer and H.-J. Timpe, Heterocycles 1991, 32, 649.
40. T. Kappe and W. Stadlbauer, Molecules 1996, 1, 255; Y. Nakagawa and R. Schäfer, Angew. Chem. Int. Ed. Engl. 1999, 38, 1083; J. Y. Chang, T. J Kim, M. J. Han and K. H. Chae, Polymer 1999, 40, 4049.
41. T. Kappe and W. Stadlbauer, Molecules 1996, 1, 255; Y. Nakagawa and R. Schäfer, Angew. Chem. Int. Ed. Engl. 1999, 38, 1083; J. Y. Chang, T. J Kim, M. J. Han and K. H. Chae, Polymer 1999, 40, 4049.
42. T. Kappe and W. Stadlbauer, Molecules 1996, 1, 255; Y. Nakagawa and R. Schäfer, Angew. Chem. Int. Ed. Engl. 1999, 38, 1083; J. Y. Chang, T. J Kim, M. J. Han and K. H. Chae, Polymer 1999, 40, 4049.
43. D. J. am Ende, K. M. DeVries, P.J. Clifford and S.J. Brenek, Org. Proc. Res. & Dev. 1998, 2, 382.
44. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
45. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
46. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
47. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
48. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
49. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
50. P. Spagnolo and P. Zanirato, J. Org. Chem. 1978, 43, 3539; D. Spinelli and P. Zanirato, J. Chem. Soc. Perkin Trans. 2 1993, 1129; S. Gronowitz and P. Zanirato J. Chem. Soc. Perkin Trans. 2 1994, 1815; M.T. Di Gioia, E. Foresti, D. Nanni and P. Zanirato, Gazz. Chim. Ital. 1995, 125, 151; D. Spinelli and P. Zanirato, Chim. Ind. (Milan), 1996, 78, 953; P. Spagnolo and P. Zanirato, J. Chem. Soc. Perkin Trans 1 1996, 963; D. Nanni and P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1997, 1003; ref. 6f.
51. T. L. Gilchrist, Adv. Heterocycl. Chem. 1987, 41, 67; E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand. 1993, 47, 244.
52. T. L. Gilchrist, Adv. Heterocycl. Chem. 1987, 41, 67; E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand. 1993, 47, 244.
53. T. L. Gilchrist, Adv. Heterocycl. Chem. 1987, 41, 67; E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand. 1993, 47, 244.
54. T. L. Gilchrist, Adv. Heterocycl. Chem. 1987, 41, 67; E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand. 1993, 47, 244.
55. P. A. S. Smith, Aryl and Heteroaryl Azides and Nitrenes, in Azides and Nitrenes: Reactivity and Utility, ed. E. F. V. Scriven, Academic Press, New York, 1984, pp. 182-193; L. K. Dyall, P. M. Suffolk, W. Dehaen and G. L'abbé, J. Chem. Soc. Perkin Trans. 2 1994, 2115; E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens and W. Dehaen, Tetrahedron 1997, 28, 9657.
56. P. A. S. Smith, Aryl and Heteroaryl Azides and Nitrenes, in Azides and Nitrenes: Reactivity and Utility, ed. E. F. V. Scriven, Academic Press, New York, 1984, pp. 182-193; L. K. Dyall, P. M. Suffolk, W. Dehaen and G. L'abbé, J. Chem. Soc. Perkin Trans. 2 1994, 2115; E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens and W. Dehaen, Tetrahedron 1997, 28, 9657.
57. P. A. S. Smith, Aryl and Heteroaryl Azides and Nitrenes, in Azides and Nitrenes: Reactivity and Utility, ed. E. F. V. Scriven, Academic Press, New York, 1984, pp. 182-193; L. K. Dyall, P. M. Suffolk, W. Dehaen and G. L'abbé, J. Chem. Soc. Perkin Trans. 2 1994, 2115; E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens and W. Dehaen, Tetrahedron 1997, 28, 9657.
58. Hazard is associated with thermal reaction of carbonyl azides, see: P.A.S. Smith, Organic Reactions, Wiley, London, 1946, 337; Bretherick's Reactive Chemical Hazard Database, Butterworth-Heineman, P. Urban, ed., Oxford, 1999.
59. Hazard is associated with thermal reaction of carbonyl azides, see: P.A.S. Smith, Organic Reactions, Wiley, London, 1946, 337; Bretherick's Reactive Chemical Hazard Database, Butterworth-Heineman, P. Urban, ed., Oxford, 1999.
60. D. Binder, G. Habison and C. R. Noe, Synthesis 1977, 255.
61. A. Padwa and T. Wu, ARKIVOC, 2000, 1, 193.
62. R. S. Treptow, J. Chem. Educ. 1995, 72, 499; J. Güèmez, S. Velasco and M. A. Matìas, J. Chem. Educ. 1995, 72. 199.
63. R. S. Treptow, J. Chem. Educ. 1995, 72, 499; J. Güèmez, S. Velasco and M. A. Matìas, J. Chem. Educ. 1995, 72. 199.
64. Yu. K. Yur'ev and N. K. Sadovaya, J. Gen. Chem. U.S.S.R. 1964, 34, 1814; B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988, 89.
65. Yu. K. Yur'ev and N. K. Sadovaya, J. Gen. Chem. U.S.S.R. 1964, 34, 1814; B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988, 89.
66. D. W. Knight and A. P. Nott, Tetrahedron Lett. 1980, 21, 5051.
67. a) M. N. Belgacem, J. Quillerou, A. Gandini, J. Rivero and G. Roux, Eur. Polym. J. 1989, 25, 1125;
68. b) M. Toselli and P. Zanirato, J. Chem. Soc. Perkin 1 1992, 1101.