Conformational studies by dynamic NMR. 66. Ring inversion in a cyclic disilane: 1,1,4,4-tetramethyl-1,4-disilacyclohexane

Tetrahedron

Volumn 54, Issue 43, 1998, Pages 13181-13184

  Casarini, Daniele ^a   Lunazzi, Lodovico ^a   Mazzanti, Andrea ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

EID: 0032558634     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00799-6     Document Type: Article

References (17)

1. (1) Part 65. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 4991.
2. (2) In partial fulfilment of the Ph.D. requirements in Chemical Sciences, University of Bologna.
3. (3) Bushweller, C. H.; O'Neil, J. W.; Bilofsky, H. S. Tetrahedron 1971, 27, 3065. See also: Jensen, F. R.; Bushweller, C. H Tetrahedron Lett. 1968, 2825.
4. (3) Bushweller, C. H.; O'Neil, J. W.; Bilofsky, H. S. Tetrahedron 1971, 27, 3065. See also: Jensen, F. R.; Bushweller, C. H Tetrahedron Lett. 1968, 2825.
5. (4) Dalling, D. K.; Grant, D. M.; Johnson, L. F. J. Am. Chem. Soc. 1971, 93, 3678.
6. (5) Murray, R. W.; Kaplan, M. L. Tetrahedron 1967, 23, 1575. See also: Friebolin, H.; Faisst, W.; Schmid, H.G.; Kabuss, S. Tetrahedron Lett. 1966, 1317.
7. (5) Murray, R. W.; Kaplan, M. L. Tetrahedron 1967, 23, 1575. See also: Friebolin, H.; Faisst, W.; Schmid, H.G.; Kabuss, S. Tetrahedron Lett. 1966, 1317.
8. (6) Murray, R. W.; Kaplan, M. L. Tetrahedron 1969, 25, 1651.
9. (7) This assignment is not unambiguous because, in analogy with methyl cyclohexanes, the signal of the silicon bonded methyl carbon in the axial position has been assumed to be upfield to its equatorial partner. See: Dalling, D. K.; Grant, D. M. J. Am. Chem. Soc. 1967, 89, 6612. Anet, F. A. L.; Bradley, C. N.; Buchanan, G. W. J. Am. Chem. Soc. 1971, 93, 258. Booth, H.; Everett, J. R. J. Chem. Soc., Perkin Trans. 2 1980, 255.
10. (7) This assignment is not unambiguous because, in analogy with methyl cyclohexanes, the signal of the silicon bonded methyl carbon in the axial position has been assumed to be upfield to its equatorial partner. See: Dalling, D. K.; Grant, D. M. J. Am. Chem. Soc. 1967, 89, 6612. Anet, F. A. L.; Bradley, C. N.; Buchanan, G. W. J. Am. Chem. Soc. 1971, 93, 258. Booth, H.; Everett, J. R. J. Chem. Soc., Perkin Trans. 2 1980, 255.
11. (7) This assignment is not unambiguous because, in analogy with methyl cyclohexanes, the signal of the silicon bonded methyl carbon in the axial position has been assumed to be upfield to its equatorial partner. See: Dalling, D. K.; Grant, D. M. J. Am. Chem. Soc. 1967, 89, 6612. Anet, F. A. L.; Bradley, C. N.; Buchanan, G. W. J. Am. Chem. Soc. 1971, 93, 258. Booth, H.; Everett, J. R. J. Chem. Soc., Perkin Trans. 2 1980, 255.
12. -1 higher.
13. (9) Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Okazaki, R.; Yamamoto, G. J. Am. Chem. Soc. 1990, 112, 2915. Anderson, J. E.; Tocher, D. A.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1991, 56, 1731. Lunazzi, L.; Casarini, D.; Cremonini, M. A.; Anderson, J. E. Tetrahedron 1991, 47, 7465. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
14. (9) Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Okazaki, R.; Yamamoto, G. J. Am. Chem. Soc. 1990, 112, 2915. Anderson, J. E.; Tocher, D. A.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1991, 56, 1731. Lunazzi, L.; Casarini, D.; Cremonini, M. A.; Anderson, J. E. Tetrahedron 1991, 47, 7465. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
15. (9) Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Okazaki, R.; Yamamoto, G. J. Am. Chem. Soc. 1990, 112, 2915. Anderson, J. E.; Tocher, D. A.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1991, 56, 1731. Lunazzi, L.; Casarini, D.; Cremonini, M. A.; Anderson, J. E. Tetrahedron 1991, 47, 7465. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
16. (9) Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Okazaki, R.; Yamamoto, G. J. Am. Chem. Soc. 1990, 112, 2915. Anderson, J. E.; Tocher, D. A.; Casarini, D.; Lunazzi, L. J. Org. Chem. 1991, 56, 1731. Lunazzi, L.; Casarini, D.; Cremonini, M. A.; Anderson, J. E. Tetrahedron 1991, 47, 7465. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
17. (10) Courtesy of Prof. F. Gasparrini, University "La Sapienza", Rome.