Cleavage of Si-Ar bond vs Si-Me bond: A remarkable counterion effect on reactivity

Chemical Communications

Volumn , Issue 17, 2002, Pages 1924-1925

  Tipparaju, Suresh Kumar ^a   Mandal, Sunil K ^a,b   Sur, Surojit ^a   Puranik, Vedavati G ^a   Sarkar, Amitabha ^a,c  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b UNIVERSITY OF UTAH   (United States)

^c DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; OXIDE; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL PARAMETERS; SYNTHESIS;

EID: 0036967749     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b205373j     Document Type: Article

References (22)

1. (a) S. K. Mandal and A. Sarkar, J. Org. Chem., 1998, 63, 1901;
2. (b) S. K. Mandal and A. Sarkar, J. Org. Chem., 1998, 63, 5672.
3. (a) W. H. Moser, K. E. Endsley and J. T. Colyer, Org. Lett., 2000, 2, 717;
4. (b) W. H. Moser, J. Zhang, C. S. Lecher, T. L. Frazier and M. Pink, Org. Lett., 2002, 4, 1981.
5. Review: W. H. Moser, Tetrahedron, 2001, 57, 2065.
6. For an account, see: A. Sarkar, S. Ganesh, S. Sur, S. K. Mandal, V. M. Swamy, B. C. Maity and T. Sureshkumar, J. Organomet. Chem., 2001, 624, 18.
7. All compounds reported herein are racemic complexes, only one enantiomer is depicted in the schemes to illustrate the chemistry. Yields refer to isolated yields of purified products.
8. The stereochemical assignments in the present paper are based on close similarity of spectral data among the analogs of 2a and 2′ and crystal structure of an analog of 2a that have been recently reported: S. Sur, S. K. Mandal, S. Ganesh, V. G. Puranik and A. Sarkar, Indian J. Chem., Sect. B, 2001, 40, 1063.
9. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
10. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
11. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
12. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
13. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
14. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
15. For examples of cyclization by reaction of oxygen nucleophile on a trimethylsilyl group, see: (a) Y. M. Hijji, P. F. Hudrlik and A. M. Hudrlik, Chem Commun., 1998, 1213; (b) P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747; (c) Y. Yamamoto, Y. Takeda and K. Akiba, Tetrahedron Lett., 1989, 30, 725; (d) W. Kirmse and F. Soellenboehmer, J. Chem. Soc., Chem. Commun., 1989, 774; (e) K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090; (f) M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859; (g) H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nozaki, Tetrahedron., 1985, 41(16), 3257.
16. 2. CCDC 187534. See http://www.rsc.org/suppdata/cc/b2/b205373j/ for crystallographic files in cif or other electonic format
17. (b) G. M. Sheldrick, SHELX-97 program for crystal structure solution and refinement, University of Goettingen, Germany, 1997.
18. For an extensive collection of references including reviews on hypervalent silicon and other elements, see: T. Kawashima, K. Naganuma and R. Okazaki, Organometallics, 1998, 17, 367.
19. E. W. Colvin, in Silicon in Organic Synthesis, Butterworths, 1981, p. 42.
20. We have found that tricarbonylchromium plays no role in this cyclization. Uncomplexed substrates also similarly cyclize in the presence of magnesium counterion (Suresh Kumar Tipparaju, unpublished results).
21. 2OH] leads to Brook product, while magnesium alkoxide promotes cyclization (Suresh Kumar Tipparaju, unpublished results)
22. J. Wong, K. A. Sannes, C. E. Johnson and J. I. Brauman, J. Am. Chem. Soc, 2000, 122, 10878.