Rearrangement of o-(chloromethyldimethylsilyl)phenylmethoxide: Evidence for an apical position of the migrating group in a trigonal bipyramid intermediate

Chemical Communications

Volumn , Issue 11, 1998, Pages 1213-1214

  Hijji, Yousef M ^a,b   Hudrlik, Paul F ^a   Hudrlik, Anne M ^a  

^a HOWARD UNIVERSITY   (United States)

^b MORGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012807196     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a801377b     Document Type: Article

References (14)

1. For leading references, see P. F. Hudrlik, Y. M. Abdallah, A. K. Kulkarni and A. M. Hudrlik, J. Org. Chem., 1992, 57, 6552.
2. P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6743 and references cited therein.
3. R. Damrauer, V. E. Yost, S. E. Danahey and B. K. O'Connell, Organometallics, 1985, 4, 1779.
4. S. L. Aprahamian and H. Shechter, Tetrahedron Lett., 1990, 31, 1089.
5. Although not simultaneously for reactions proceeding with retention of stereochemistry: R. R. Holmes, Chem. Rev., 1990, 90, 17;
6. A. R. Bassindale and P. G. Taylor, in The Chemistry of Organic Silicon Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1989, part 1, pp. 839-892.
7. I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063.
8. P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747.
9. Y. M. Hijji, P. F. Hudrlik, C. O. Okoro and A. M. Hudrlik, Synth. Commun., 1997, 27, 4297.
10. E. Baciocchi, R. Bernini and O. Lanzalunga, J. Chem. Soc., Chem. Commun., 1993, 1691.
11. For other examples of cleavage at silicon by intramolecular alkoxide, see: C. Rücker, Tetrahedron Lett., 1984, 25, 4349;
12. W. Kirmse and F. Söllenböhmer, J. Chem. Soc., Chem. Commun., 1989, 774.
13. Nucleophilic substitution reactions at silicon are felt to occur via apical entry, and although pseudorotation of the pentacoordinate intermediate is possible, oxygen is more apicophilic than carbon. See ref. 5 and C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371;
14. R. R. Holmes, Chem. Rev., 1996, 96, 927.