Polymer-mediated pinacol rearrangements

Synlett

Volumn , Issue 15, 2011, Pages 2191-2194

  Pavlik, Christopher ^a   Morton, Martha D ^a   Smith, Michael B ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

diol; PEDOT; pinacol; poly(pyrrole); rearrangement

Indexed keywords

ALDEHYDE; HYDROCARBON; INORGANIC ACID; KETONE; LEWIS ACID; ORGANIC SOLVENT; POLY(3,4 ETHYLENEDIOXYTHIOPHENE); POLYMER; POLYPYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; FILTRATION; POLYMERIZATION; QUANTUM YIELD; STOICHIOMETRY;

EID: 80052670503     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261148     Document Type: Article

References (62)

1. Fittig R, Annalen 1860 114 54
2. Collins C J., Quart. Rev. Chem. Soc. 1960 14 357
3. Mundy B P., Otzenberger R D., J. Chem. Educ. 1971 48 431
4. The Merck Index 14th ed. Merck Whitehouse Station (NJ) 2006 ONR-74
5. Mundy B P., Ellerd M G., Favaloro F G. Jr., Name Reactions and Reagents in Organic Synthesis 2nd ed. Wiley-Interscience New Jersey 2005 514-516
6. For a reaction initiated by iminium salts, see
7. Lopez L, Mele G, Mazzeo C, J. Chem. Soc., Perkin Trans. 1 1994 779
8. de Sanabia J A., Carrión A E., Tetrahedron Lett. 1993 34 7837
9. Harada T, Mukaiyama T, Chem. Lett. 1992 81
10. De Lezaeta M, Sattar W, Svoronos P, Karimi S, Subramaniam G, Tetrahedron Lett. 2002 43 9307
11. Corey E J., Danheiser R L., Chandrasekaran S, J. Org. Chem. 1976 41 260
12. Yang Z.-Y, Wang L, Drysdale N, Doyle M, Sun Q, Choi S K., Angew. Chem. Int. Ed. 2003 42 5462
13. Harmer M A., Sun Q, Appl. Catal. A 2001 221 45
14. Souzy R, Ameduri B, Boutevin B, Capron P, Marsacq D, Gebel G, Fuel Cells 2005 3 383
15. Gelbard G, Ind. Eng. Chem. Res. 2005 44 8468
16. Kirchmer S, Reuter K, J. Mater. Chem. 2005 15 2077
17. Greczynski G, Kugler T, Keil M, Osikowicz W, Fahlman M, Salaneck W, J. Electron Spectrosc. Relat. Phenom. 2001 121 1
18. Groenendaal L, Jonas F, Freitag D, Pielartzik H, Reynolds J, Adv. Mater. 2000 12 481
19. Brezoi D.-V, J. Sci. Arts 2010 53
20. Wolken J J., Light Detectors, Photoreceptors, and Imaging Systems in Nature Oxford University Press New York 1995
21. Tourillon G, In Handbook of Conducting Polymers Vol. 1 Skotheim T A. Marcel Dekker New York 1986 293-350
22. Vernitskaya T V., Efimov O N., Russ. Chem. Rev. 1997 66 443
23. Grande H, Otero T F., Rodriguez J, In Electrical and Optical Polymer Systems: Fundamentals, Methods, and Applications Wise D L. Marcel Dekker New York 1998 17-46
24. Corradi R, Armes S P., Synth. Met. 1997 84 453, Reuter K, Kirchmeyer S, JP 2003261573 2003, Reuter K, Kirchmeyer S, US 2003139505 2003, Jonas F, Wolf G.-D, EP 0553671 1993, Jonas F, Karbach A, Muys B, van Thillo E, Wehrmann R, Elschner A, Dujardin R, EP 0686662 1995, Jonas F, Guntermann U, Lerch K, Boehnke A, Basten H, Thometzek P, US 5792558 1996
25. DAngelo J G., Sawyer R, Kumar A, Onorato A, McCluskey C, Delude C, Vollenweider L, Reyes N, French R, Warner S, Chou J, Stenzel J, Sotzing G A., Smith M B., J. Polym. Sci., Part A: Polym. Chem. 2007 45 2328
26. DAngelo J G., Kumar A, Onorato A, Delude C J., Sotzing G A., Smith M B., Polymer 2007 48 4328
27. Onorato A, Invernale M A., Berghorn I D., Pavlik C, Sotzing G A., Smith M B., Synth. Met. 2010 160 2284
28. Onorato A, Pavlik C, Invernale M A., Berghorn I D., Sotzing G A., Morton M D., Smith M B., Carbohydr. Res. 2011 346 1662
29. Hill G A., Flosdorg E W., Org. Synth., Coll. Vol. I 1941 462
30. Zimmerman H, Schuster D I., J. Am. Chem. Soc. 1962 84 4527
31. Amedio J C. Jr., Bernard P J., Fountain M, Van Wagenen G Jr., Synth. Commun. 1998 28 3895
32. Stevens C, Holland W, J. Org. Chem. 1958 23 781
33. Ciminale F, Lopez L, Nacci A, DAccolti L, Vitale F, Eur. J. Org. Chem. 2005 1597
34. Bian Y, Jia Z, Youji Huaxue 2009 29 975
35. Sands R D., J. Org. Chem. 1994 59 468
36. Kita Y, Yosida Y, Mihara S, Furukawa A, Higuchi K, Fang D.-F, Fujioka H, Tetrahedron 1998 54 14689
37. Griffin C E., Hager R B., J. Org. Chem. 1963 26 599
38. Bartlett P D., Pöckel I, J. Am. Chem. Soc. 1937 59 820
39. Buton C A., Carr C D., J. Chem. Soc. 1963 5854
40. Nametkin S, Delektrosky N, Ber. Dtsch. Chem. Ges. 1924 57 583
41. Meerwein H, Justus Liebigs Ann. Chem. 1939 542 123
42. Smith W B., Bowman R E., Kmet T J., J. Am. Chem. Soc. 1959 81 997
43. Zaugg H E., Freifelder M, Horrom B W., J. Org. Chem. 1950 15 1191
44. Lyle R E., Lyle G G., J. Org. Chem. 1953 18 1058
45. Burger A, Bennet W B., J. Am. Chem. Soc. 1950 72 5414
46. Chandrasekhar S, Narsihmulu Ch, Shameem S S., Reddy N, Chem. Commun. 2003 14 1716
47. Boudjouk P, Park M, So J, J. Org. Chem. 1988 53 5871
48. Fürstner A, Csuk R, Rohrer C, Weidmann H, J. Chem. Soc., Perkin Trans. 1 1988 1729
49. Periasamy M, Ramani G, Muthukumaragopal G P., Synthesis 2009 1739
50. Clerici A, Pastori N, Porta O, Eur. J. Org. Chem. 2002 3326
51. Waser J, Carreira E M., Angew. Chem. Int. Ed. 2004 43 4099
52. Meerwin H, Justus Liebigs Ann. Chem. 1939 542 123
53. Hine J, McMahon R, Roberts J, J. Am. Chem. Soc. 1950 72 4237
54. Kim S, Osakada K, Takeuchi D, J. Am. Chem. Soc. 2002 124 762
55. Hu Y, Wang J, Xi Y, Gu S, Synth. Commun. 1998 28 3299
56. Roussis V, Gloer K, Wiemer D, J. Org. Chem. 1988 53 2011
57. Meerwein H, Muhlendyk W, Justus Liebigs Ann. Chem. 1914 405 129; see p. 174
58. Cavdar H, Saracoglu N, Tetrahedron 2009 65 985
59. Corey E J., Clark D A., Goto G, Marfat A, Mioskowski C, Samuelsson B, Hammarstroem S, J. Am. Chem. Soc. 1980 102 1436
60. Wong J C. Y., Lacombe P, Sturino C F., Tetrahedron Lett. 1999 40 8751
61. Guerlavais V, Carroll P J., Joullie M M., Tetrahedron: Asymmetry 2002 13 675
62. Yoon J, Cram D J., J. Am. Chem. Soc. 1997 119 11796