The synthesis and characterization of a new family of polyamide dendrimers

Chemistry - A European Journal

Volumn 4, Issue 5, 1998, Pages 781-795

  Ashton, Peter R ^a   Anderson, Derek W ^b   Brown, Christopher L ^a   Shipway, Andrew N ^a   Stoddart, J Fraser ^a,c   Tolley, Malcolm S ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b DEFENCE SCIENCE AND TECHNOLOGY LABORATORY   (United Kingdom)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino; Branched monomers; Copolymerizations; Dendrimers; Polyacids; Polymers

Indexed keywords

EID: 0031781711     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980515)4:5<781::AID-CHEM781>3.0.CO;2-3     Document Type: Article

References (100)

1. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
2. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
3. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
4. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
5. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
6. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
7. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
8. A search of the Science Citation Index with the keyword dendrimer reveals hits for the last five years as follows: 1991, 3; 1992, 11; 1993, 19; 1994, 30; 1995, 36; 1996, 60. For recent reviews concerning dendrimers, see: a) H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem. 1992, 104, 1609-1614; Angew. Chem, Int. Ed. Engl. 1992, 31, 1571-1576; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, Aldrichimica Acta 1992, 25, 31 -38; c) D. A. Tomalia, Adv. Mater. 1994, 6, 529-539; d) G. R. Newkome, C. N. Moorefield in Comprehensive Supramolecular Chemistry, Vol.10 (Ed.: D. N. Reinhoudt), Pergamon, Oxford, UK, 1996, 777-832; e) J. M. J. Fréchet, C. J. Hawker in Comprehensive Polym. Sci. (Eds.: S. L. Aggarwal, S. Russo), 1996, 140-201; f) G. R. Newkome, C. N. Moorefield, F. Vögue in Dendritic Molecules, VCH, Weinheim, Germany, 1996; g) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci. 1998, 23, 1-56.
9. D. A. O'Sullivan, Chem. Eng. News 1993, August 16, 20-23; the PAMAM dendrimers are commercially available through Aldrich.
10. H. Brunner, J. Organomet. Chem. 1995, 500, 39-46.
11. a) J. R. Robinson, G. M. Mlynek, Adv. Drug Deliv. Rev. 1995, 16, 45 50;
12. b) A. E. Beezer, J. C. Mitchell, R. M. Colegate, D. J. Scally, L. J. Twyman, R. J. Willson, Thermochim. Acta. 1995, 277-283;
13. c) K. Sheldon, D. Liu, J. Ferguson, J. Gariépy, Proc. Nati Acad. Sci. USA 1995, 92, 2056-2060.
14. a) D. A. Tomalia, P. R. Dvornic, Nature 1994, 372, 617-618;
15. b) J. Alper, Science 1991, 251. 1562-1564.
16. a) D. A. Tomalia, M. Hall, D. M. Hedstrand, J. Am. Chem. Soc. 1987, 109. 1601-1603;
17. b) A. M. Naylor, W. A. Goddard III, G. E. Kiefer, D. A. Tomalia, ibid. 1989, 111, 2339-2341.
18. a) J. F. G. A. Jansen, R. A. J. Janssen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Adv. Mater. 1995, 7, 561-564;
19. b) K. L. Wooley, C. J. Hawker, J. M. Pochan, J. M. J. Fréchet, Macromolecules 1993, 26, 1514-1519;
20. c) G. R. Newkome, C. N. Moorefield, J. M. Keith, G. R. Baker, G. H. Escamilla, Angew. Chem. 1994, 106, 701-703; Angew. Chem. Int. Ed. Engl. 1994, 33, 666-668:
21. c) G. R. Newkome, C. N. Moorefield, J. M. Keith, G. R. Baker, G. H. Escamilla, Angew. Chem. 1994, 106, 701-703; Angew. Chem. Int. Ed. Engl. 1994, 33, 666-668:
22. d) G. R. Newkome, C. N. Moorefield, G. R. Baker, R. K. Behera, G. H. Escamilla, M. J. Sanders, ibid. 1992, 104, 901-903 and 1992, 31, 917-919;
23. d) G. R. Newkome, C. N. Moorefield, G. R. Baker, R. K. Behera, G. H. Escamilla, M. J. Sanders, ibid. 1992, 104, 901-903 and 1992, 31, 917-919;
24. e) D. A. Tomalia, A. M. Naylor, W. A. Goddard III, ibid. 1990, 102, 119-157 and 1990, 29, 138-175.
25. e) D. A. Tomalia, A. M. Naylor, W. A. Goddard III, ibid. 1990, 102, 119-157 and 1990, 29, 138-175.
26. R. F. Service, Science 1995, 267, 458-459.
27. G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180.
28. G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180.
29. M. F. Ottaviani, S. Bossmann, N. J. Turro, D. A. Tomalia, J. Am. Chem. Soc. 1994, 116, 661-671.
30. D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Polym. J. 1985, 17, 117-132.
31. C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Am. Chem. Soc. 1993, 115, 4375-4376.
32. M. L. Mansfield, L. I. Klushin, Macromolecules 1993, 26, 4262-4268.
33. C.J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1990, 112, 7638-7647.
34. Many dendrimer syntheses rely on the so-called divergent approach and date back to the seminal paper demonstrating the feasibility of dendrimer synthesis. See: E. Buhleier, W. Wehner, F. Vögtle, Synthesis 1978, 155-158.
35. M. L. Mansfield, Macromolecules 1993, 26, 3811-3814.
36. K. L. Wooley, C.J. Hawker, J. M. J. Fréchet. J. Chem. Soc. Perkin Trans. 1 1991, 1059-1076.
37. J. M. J. Fréchet, C. J. Hawker, K. L. Wooley, J. Macromol Sci. Pure Appl. Chem. 1994, A31, 1627-1645.
38. a) S. Campagna, G. Denti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995, 1, 211-220;
39. b) H.-F. Chow, C. C. Mak, J. Chem. Soc. Perkin Trans, 1 1994, 2223-2228;
40. c) N. Launay, A.-M. Caminade. J.-P. Majoral, J. Am. Chem. Soc. 1995, 777, 3282-3283;
41. d) A. Rajca, S. Utamapanya, ibid. 1993, 115, 10688-10694;
42. e) S. Achar, R. J. Puddephatt, J. Chem .Soc. Chem. Commun. 1994, 1895-1896;
43. f) R. H. E. Hudson, M. J. Damha, J. Am. Chem. Soc. 1993, 115, 2119-2124;
44. g) D. Seyferth, D. Y. Son, A. L. Rheingold, R. L. Ostrander, Organometallics 1994, 13, 2682-2690.
45. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261.
46. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. Int. 1994, 106, 123-126: Angew. Chem. Int. Ed. Engl. 1994, 106, 82-85.
47. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. Int. 1994, 106, 123-126: Angew. Chem. Int. Ed. Engl. 1994, 106, 82-85.
48. R. Spindler, J. Chem. Soc. Perkin Trans, 1 1993, 913- 918.
49. T. Kawaguchi, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1995, 117, 2159-2165.
50. For an exception to this rule, see: R. Spindler, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans, 1 1993, 913-918.
51. C. J. Hawker, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans, 1 1992, 2459-2469.
52. a) H.-F. Chow, C. C. Mak, J. Chem. Soc. Perkin Trans. 1 1994, 2223-2228;
53. b) S. Achar, R. J. Puddephatt, Organometallics 1995, 14, 1681 -1687;
54. c) D. Seyferth, D. Y. Son, ibid. 1994, 13, 2682-2690;
55. d) K. Rengan, R. Engel, J. Chem. Soc. Perkin Trans, 1 1991, 987-990.
56. a) E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1993, 32, 1370-1372; Angew. Chem. Int. Ed. Engl. 1993, 32, 1308-1311;
57. a) E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1993, 32, 1370-1372; Angew. Chem. Int. Ed. Engl. 1993, 32, 1308-1311;
58. b) N. Launay, A. M. Caminade, J.-P Majoral, J. Am. Chem. Soc. 1995, 117, 3282-3283.
59. a) G. R. Newkome, V. V. Narayanan, A. K. Patri, J. Gross, C. N. Moorefield, G. R. Baker, Proc. ACS Division of Polymeric Materials: Sci. Eng. 1995, 73, 222-223;
60. b) A. Rajca, S. Utamapanya, J. Am. Chem. Soc. 1993, 115, 10688-10694;
61. c) T. Nagasaki, O. Kimura, M. Ukon, S. Arimori, I. Hamachi, S. Shinkai, J. Chem. Soc. Perkin Trans, 1 1994, 75-81;
62. d) H. Uchida, Y. Kabe, K. Yoshino, A. Kawamata, T. Tsumuraya, S. Masumune, J. Am. Chem. Soc. 1990, 112, 7077-7079.
63. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. Int. Ed. Engl. 1994, 33, 82-85.
64. a) T. Kawaguchi, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc, 1995, 117, 2159-2165;
65. b) A. Miedaner, C. J. Curtis, R. M. Barkley, D. L. DuBois, Inorg. Chem. 1994, 33, 5482-5490.
66. C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1992, 114, 8405-8413.
67. E. H. Gold, E. Babad, J. Org. Chem. 1972, 37, 2208-2210.
68. a) E. Amble, J. Dale, Acta Chem. Scand. 1979, 33, 698-700;
69. b) P. J. Maurer, H. Takahata, H. Rapoport, J. Am. Chem. Soc. 1984, 106, 1095-1098;
70. c) T. Hamada. J. Am. Chem. Soc. 1986, 108, 140-145;
71. d) W. Yuan, K. Fearon, M. H. Gelb, J. Org. Chem. 1989, 54. 906-910.
72. a) S. J. Blarer, D. Seebach, Chem. Ber. 1983, 116, 2250;
73. b) T. P. Curran, M. P. Pollastri, S. M. Abelleira, R. J. Messier, T. A. McCollum, C. G. Rowe, Tetrahedron Lett. 1994, 35, 5409-5412.
74. L. Qian, Z. Sun, M. P. Mertes, K. B. Mertes, J. Org. Chem. 1991, 56, 4904-4907.
75. A. Zwierak, K. Osowska, Synthesis 1984, 223-224.
76. a) S. K. Banerjee, B. D. Gupta, K. Singh, J. Chem. Soc. Chem. Commun. 1982, 815-816;
77. b) H.E. Zaugg, J. Org. Chem. 1976, 41, 3419-3421.
78. A. N. Shipway, J. F. Stoddart, unpublished results.
79. R. G. Denkewalter, J. Kolc, W. J. Luskasavage, US Patent 4289872, 1981.
80. L. J. Twyman, A. E. Beezer, J. C. Mitchell, Tetrahedron Lett. 1994, 35, 4423-4424.
81. T. Nagasaki, O. Kimura, M. Ukon, I. Hamachi, S. Shinkai, J. Chem. Soc. Perkin Trans, 1 1994, 75-81.
82. K. E. Uhrich, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans, 1 1992, 1623-1630.
83. P. J. Dandliker, F. Diederich, M. Gross, C.B. Knobler, A. Louati, E. M. Sanford, Angew. Chem. 1994, 106, 1821 -1824; Angew. Chem. Int. Ed. Engl. 1994, 33, 1739-1742.
84. P. J. Dandliker, F. Diederich, M. Gross, C.B. Knobler, A. Louati, E. M. Sanford, Angew. Chem. 1994, 106, 1821 -1824; Angew. Chem. Int. Ed. Engl. 1994, 33, 1739-1742.
85. An aliquot (39 mg) of the crude reaction mixture, which contained 34 mg of dendritic materials with respect to the starting amine, was estimated by GPC to contain 10.9 mg of sixth-generation products.
86. a) B. L. Schwartz, A. L. Rockwood, R. D. Smith, D. A. Tomalia, R. Spindler, Rapid Commun. Mass Spectrom. 1995, 9, 1552- 1555;
87. b) P. R. Dvornic, D. A. Tomalia, Macromol Symp. 1995, 95, 403-428;
88. c) J. W. Leon, J. M. J. Fréchet, Polym. Bull. 1995, 35, 449-455.
89. M. J. Maciejewski, J. Macromol. Sci. Chem. 1982, A17(4), 689-703.
90. The fourth-generation dendrimer carries four times the number of end groups and has twice the arm length (hence four times the surface area) of its second-generation analogue. The transformation from a free to a globular dendrimer conformation is usually associated with an increase in the end group :surface area ratio.
91. e is the elution volume, and a and b are constants.
92. D. A. Tomalia, V. B. M. Hall, D. M. Hedstrand, Macromolecules 1987, 20, 1167-1169.
93. c.
94. a) P. R. Ashton, S. E. Boyd, C. L. Brown, N. Jayaraman, S. A. Nepogodiev, J. F. Stoddart, Chem. Eur. J. 1996, 2, 1115-1128;
95. b) M. Murat, G. S. Grest, Macromolecules 1996, 29, 1278-1285.
96. -1. Structures used to describe conformations of the dendrimers at 300 K were taken from the end of the 20 ps equilibration period. Radii of the dendrimers were measured from within CSC Chem 3D pro by the averaging of about ten core-to-surface distances.
97. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson. W. C. Still, J. Comp. Chem. 1990, 11, 440-467.
98. The sixth-generation contains 63 double-branched building blocks, 21 times the number (3) in the second-generation dendrimer. The sixth-generation dendrimer has three times the radius of the second-generation dendrimer, however, giving it 27 times the available volume in which to accommodate only 21 times the number of moieties.
99. The ninhydrin reagent was prepared with ninhydrin (0.3 g) and glacial acetic acid (3 mL) in n-butanol (100 mL).
100. The cerium reagent was prepared with phosphomolybdic acid (2.5 g), cerium(IV) sulfate (1.0 g), and sulfuric acid (6 mL) in water (100 mL).