Probing the influence of stereoelectronic effects on lithium affinity in 1,3- and 1,4-dioxa systems

Journal of Physical Organic Chemistry

Volumn 14, Issue 7, 2001, Pages 488-494

  Ganguly, Bishwajit ^a   Fuchs, Benzion ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Acetals; Anomeric effect; Gauche effect; Lithium affinity; Stereoelectronic effects; Tetraoxadecalin

Indexed keywords

EID: 0035397453     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.397     Document Type: Article

References (58)

1. (a) Thatcher GRJ (ed). The Anomeric effect and Associated Stereoelecironic Effects ACS Symposium Series No. 539. American Chemical Society: Washington, DC. 1993;
2. (b) Juaristi E, Cuevas G. Tetrahedron 1992; 48: 5019;
3. (c) Kirby AJ. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. Springer: Berlin, 1983;
4. (d) Szarek WA, Horton D. (eds). Anomeric Effect. Origins and Consequences. ACS Symposia Series No. 87. American Chemical Society: Washington, DC, 1979;
5. (e) Deslongchamps P. Stereoelectronic Effects in Organic Chemistry. Wiley: New York, 1983;
6. (f) Lemieux RU. Pure Appl. Chem. 1971; 25: 527;
7. (g) Romers C, Altona C, Buys HR, Havinga E. Top. Stereochem. 1969; 4: 39.
8. (a) Altona C. PhD Thesis, University of Leiden, 1964; 2
9. (b) David S, Eisenstein O, Hehre WJ, Salem L, Hoffmann R. J. Am. Chem. Soc. 1973; 95: 3806.
10. (a) Reed AE, Schleyer PvR. Inorg. Chem. 1988; 27: 3969;
11. (b) Salzner U, Schleyer PvR. J. Org. Chem. 1994; 59: 2138, and references cited therein.
12. (a) Schleifer L, Senderowitz H, Aped P, Tartakovsky E, Fuchs B. Carbohydr. Res. 1990; 206: 21;
13. (b) Fuchs B, Schleifer L, Tartakovsky E. Nouv. J. Chim. 1984; 8: 275;
14. (c) Fuchs B, Ellencweig A, Tartakovsky E, Aped P. Angew. Chem., Int. Ed. Engl. 1986; 25: 287;
15. (d) Aped P, Apeloig Y, Ellencweig A, Fuchs B, Goldberg I, Karni M, Tartakovsky E. J. Am. Chem. Soc. 1987; 109: 1486;
16. (e) Aped P, Fuchs B, Schleifer L, Wolfe S. J. Comput. Chem. 1989; 10: 265;
17. (f) Senderowitz H, Aped P, Fuchs B. Helv. Chim. Acta 1990; 73: 2113; J. Comput. Chem. 1993; 14: 944; Tetrahedron. 1993; 49: 3879;
18. (f) Senderowitz H, Aped P, Fuchs B. Helv. Chim. Acta 1990; 73: 2113; J. Comput. Chem. 1993; 14: 944; Tetrahedron. 1993; 49: 3879;
19. (f) Senderowitz H, Aped P, Fuchs B. Helv. Chim. Acta 1990; 73: 2113; J. Comput. Chem. 1993; 14: 944; Tetrahedron. 1993; 49: 3879;
20. (g) Senderowitz H, Fuchs. B. J. Mol. Struct. THEOCHEM 1997; 395/396: 123.
21. (a) Wolfe S, Tel LM, Haines WJ, Robb MA, Csizmadia IG. J. Am. Chem. Soc. 1973; 95: 4863;
22. (b) Wolfe S. Acc. Chem. Res. 1972; 5: 102.
23. (a) Zefirov NS. J. Org. Chem. USSR 1974; 1147;
24. (b) Zefirov NS, Gurvich LG, Shashkov AS, Krimer MZ, Vorob'eva EA. Tetrahedron 1976; 32: 1211.
25. (a) Epiotis ND, Yates RL, Larson JR, Kirmaier CR, Bernardi FJ. J. Am. Chem. Soc. 1977; 99: 8379;
26. (b) Epiotis ND, Cherry W. Chem. Commun. 1973; 278;
27. (c) Epiotis ND. J. Am. Chem. Soc. 1973; 95: 3087.
28. Wiberg KB, Murcko MA, Laiding KE. J. Phys. Chem. 1990; 94: 6956.
29. (a) Craig NC, Chen A, Suh KH, Klee S, Mellau GC, Winnewisser BP, Winnewisser M. J. Am. Chem. Soc. 1997; 119: 4789;
30. (b) Engkvist O, Karlstrom G, Widmark PO. Chem. Phys. Lett. 1997; 265: 19.
31. (a) Senderowitz H, Linden A, Golender L, Abramson S, Fuchs B. Tetrahedron 1994; 50: 9691;
32. (b) Senderowitz H, Golender L, Fuchs B. Tetrahedron 1994; 50: 9707;
33. (c) Abramson S, Ashkenazi E, Goldberg I, Greenwald M, Jatzke H, Vardi M, Weinman S, Fuchs B. J. Chem. Soc., Chem. Commun. 1994; 1611;
34. (d) Frische K, Greenwald M, Ashkenazi E, Lemcoff NG, Abramson S, Golender L, Fuchs B. Tetrahedron Lett. 1995; 36: 9193;
35. (e) Jatzke H, Frische K, Greenwald M, Golender L, Fuchs B. Tetrahedron, 1997; 53: 4821;
36. (f) Linden A, Beckhaus H-D, Verevkin SP, Rüchardt C, Ganguly B, Fuchs B. J. Org. Chem. 1998; 63: 8205;
37. (g) Grabarnik M, Abramson S, Lemcoff NG, Madar R, Weinman S, Fuchs B. J. Org. Chem. 2000; 65: 1636.
38. (a) Ganguly B, Fuchs B. J. Org. Chem. 1997; 62: 8892;
39. (b) Ganguly B, Fuchs B. J. Org. Chem. 1999; 65: 558.
40. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA, Gaussian 94. Gaussian: Pittsburgh, PA, 1995.
41. Smith SF, Chandrasekhar J, Jorgensen WL. J. Phys. Chem. 1982; 86: 3308.
42. (a) Hay BP, Rustad JR. J. Am. Chem. Soc. 1994; 116: 6316;
43. (b) Hay BP, Rustad JR, Hostetler CJ. J. Am. Chem. Soc. 1993; 115: 11158.
44. Ponomaraev DA, Takhistov VV, J. Chem. Educ. 1997; 74: 201.
45. (a) Hill SE, Glendening ED, Feller D. J. Phys. Chem. A 1997; 101: 6125;
46. (b) More MB, Glendening ED, Ray D, Feller DF, Armentrout PB. J. Phys. Chem. A 1996; 100: 1605;
47. Smith GD, Jaffe RL, Partridge H. J. Phys. Chem. 1997; 101: 1705.
48. (a) Hill SE, Feller D, Glendening ED. J. Phys. Chem. A 1998; 102: 3813;
49. (b) Ray D, Feller DF, More MB, Glendening ED, Armentrout PB. J. Phys. Chem. A 1996; 100: 16116.
50. (a) Allen FH, Kennard O. Chem. Des. Autom. News 1993; 8: 31;
51. (b) Allen FH, Kennard O, Taylor R. Acc. Chem. Res. 1983; 16: 146.
52. (a) Staley RH, Beauchamp JL. J. Am. Chem. Soc. 1975; 97: 5920;
53. (b) Woodin RL, Beauchamp JL. J. Am. Chem. Soc. 1978; 100: 501;
54. Chem. Phys. 1979; 41: 1.
55. (a) Olmstead MM, Power PP. J. Organomet. Chem. 1991; 408: 1;
56. (b) Hikansson M, Ottosson C-H, Boman A, Johnels D. Organometallics 1998; 17: 1208.
57. (a) Rogers RD, Bynum RV, Atwood JL. J. Cryst. Spectrosc. 1984; 14: 29;
58. (b) Riffel H, Neumuller B, Fluck EZ. Anorg. Allg. Chem., 1993; 619: 1682.