Synthesis and conformational features of sym N,N′,N″- triarylguanidines

Journal of Chemical Sciences

Volumn 122, Issue 2, 2010, Pages 157-167

  Gopi, Kanniyappan ^a   Rathi, Brijesh ^a   Thirupathi, Natesan ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

AM1 calculations; Conformations; N donor ligands; Noncovalent interactions; Organocatalysts; Sym N,N ,N triarylguanidines

Indexed keywords

IONS; SINGLE CRYSTALS; SUBSTITUTION REACTIONS; X RAY DIFFRACTION;

AM1 CALCULATIONS; ANTI-CONFORMATIONS; ARYL SUBSTITUENTS; ELECTRONIC FACTORS; N-DONOR LIGANDS; NON-COVALENT INTERACTION; ORGANOCATALYSTS; SINGLE CRYSTAL X-RAY DIFFRACTION;

CONFORMATIONS;

EID: 77950213443     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-010-0017-8     Document Type: Article

References (60)

1. Ishikawa T and Kumamoto T 2006 Synthesis 737
2. Ishikawa T 2009 in Superbases for organic synthesis: Guanidines, amidines, phosphazenes and related organocatalysts, (ed) T Ishikawa (Weinheim: Wiley-VCH) Chapter 4, pp 93-136
3. Coles M P 2009 Chem. Commun. 3659
4. Edelmann F T 2008 Adv. Organomet. Chem. 57 183
5. Coles M P 2006 Dalton Trans 985
6. Bailey P J and Pace S 2001 Coord. Chem. Rev. 214 91
7. Schuchardt U, Sercheli R and Vargas R M 1998 J. Braz. Chem. Soc. 9 199
8. Costa M, Chiusoli G P, Taffurelli D and Dalmonego G 1998 J. Chem. Soc. Perkin Trans. 1 1541
9. Sercheli R, Ferreira A L B, Guerreiro M C, Vargas R M, Sheldon R A and Schuchardt U 1997 Tetrahedron Lett. 38 1325
10. (a) Eckert-Maksić M, Glasovac Z, Trošelj P, Kütt A, Rodima T, Koppel I and Koppel I A 2008 Eur. J. Org. Chem. 5176;
11. (b) Glasovac Z, Kovacevic B, Mestrovic E and Eckert-Maksić M 2005 Tetrahedron Lett. 46 8733
12. Katritzky A R and Rogovoy B V 2005 Arkivoc 4 49
13. Powell D A, Ramsden P D and Batey R A 2003 J. Org. Chem. 68 2300
14. Bailey P J, Mitchell L A and Parsons S 1996 J. Chem. Soc. Dalton Trans. 2839
15. Molina P, Aller E and Lorenzo A 2003 Synlett. 714
16. (a) Du Z, Li W, Zhu X, Xu F and Shen Q 2008 J. Org. Chem. 73 8966;
17. (b) Zhang W-X and Hou Z 2008 Org. Biomol. Chem. 6 1720;
18. (c) Rowley C N, Ong T-G, Priem J, Woo T K and Richeson D S 2008 Inorg. Chem. 47 9660
19. 20) are known but presently we are focused only on 7-12 for the reasons mentioned in the introduction
20. (a) Kim Y H and Yon G H 1983 J Chem. Soc. Chem. Commun. 715;
21. (b) Molina P, Alajarín M and Saez J 1983 Synth. Commun. 13 67
22. Macholdt-Erdniss J 1958 Chem. Ber. 91 1992
23. Dyer E and Johnson T B 1932 J. Am. Chem. Soc. 54 777
24. Petrova T D and Platonov V E 2005 J. Fluorine Chem. 126 860
25. Dworkin A, Naumann R, Seigfred C and Karty J M 2005 J. Org. Chem. 70 7605
26. Williams A and Ibrahim I T 1981 Chem. Rev. 81 589
27. Mikolajczyk M and Kielbasiński P 1981 Tetrahedron 37 233
28. (a) Convers E, Tye H and Whittaker M 2004 Tetrahedron Lett. 45 3401;
29. (b) Lee J I 1995 Bull. Korean Chem. Soc. 16 1143;
30. (c) Molina P, Alajarín M, Arques A and Sáez J 1982 Synth. Commun. 12 573
31. Rahman A K F and Nicholas K M 2007 Tetrahedron Lett. 48 6002
32. Furniss B S, Hannaford A J, Smith P W G and Tatchell A R 1989 in Vogel's textbook of practical organic chemistry (England: Addison Wesley Longman) Chapter 6, Fifth edn, p 966
33. Richter R and Ulrich H 1981 J. Org. Chem. 46 3011
34. Kurzer F and Sanderson P M 1962 J. Chem. Soc. 230
35. The crystal structure of 12 was reported recently (ref. 30) but no other information is available due to its poor yield
36. Han Y and Huynh H V 2009 Dalton Trans. 2201
37. SMART and SAINT, Versions 6.22a; Bruker AXS: Madison, WI, 1999
38. Sheldrick, G M SADABS User Guide, University of Göttingen, Göttingen, Germany, 1993
39. Sheldrick, G M SHELX-97, Program for crystal structure solution and refinement (Göttingen, Germany: University of Göttingen) 1997
40. Kemme A, Rutkis M, Eiduss J 1988 Latv PSR Zinat Akad Vestis Kim Ser. 595.
41. Monforte P, Fenech G, Basile M, Ficarra P and Silvestro A 1979 J. Heterocyclic Chem. 16 341
42. Bergmann R G and Holland A W 2002 J. Am. Chem. Soc. 124 9010
43. Yoshio K, Minoru O, Shigeo M and Takeo K 1974 Jpn. Kokai Tokkyo Koho 49, 056, 934;
44. Chemical Abstr. 81: 105060
45. Boeré R E, Boeré R T, Masuda J and Wolmershäuser G 2000 Can. J. Chem. 78 1613
46. Fujinami T, Otani N and Sakai S 1977 Synthesis 889
47. Enders E, Stendel W and Voege H, 1977 German Patent DE 2, 553, 259;
48. Chemical Abstr. 87 102054
49. Enders E and Stendel W 1977 Ger. Offen DE 2, 553, 270;
50. Chemical Abstr. 87: 68002
51. Georgieva I, Mintcheva N, Trendafilova N and Mitewa M 2001 Vib. Spectrosc. 27 153
52. Raczyńska E D, Kosińska W, Ośmialowski B and Gawinecki R 2005 Chem. Rev. 105 3561
53. Yamada T, Liu X, Englert U, Yamane H and Dronskowski R 2009 Chem. Eur. J. 15 5651
54. Göbel M and Klapötke T M 2007 Chem. Commun. 3180
55. Häfelinger G and Kuske K H 1991 in The chemistry of the amidines and imidates (eds) S Patai and Z Rappoport (Chichester: Wiley-VCH) vol. 2, chapter 1.
56. Bharatam P V, Iqbal P, Malde A and Tiwari R 2004 J. Phys. Chem. A 108 10509
57. Mansfield N E, Grundy J, Coles M P, Avent A G and Hitchcock P B 2006 J. Am. Chem. Soc. 128 13879
58. Kosturkiewicz Z, Ciszak E and Tykarska E 1992 Acta. Crystallogr Sect B: Struct Sci 48 471;
59. (b) Alcock N W, Barker J and Kilner M 1988 Acta. Crystallogr Sect C: Cryst Struct Commun 44 712
60. Nangia A 2008 Acc. Chem. Res. 41 595