Control factors of two reaction modes of pentacoordinate 1,2-oxasiletanides, the peterson reaction and homo-brook rearrangement

Chemistry Letters

Volumn , Issue 11, 1999, Pages 1139-1140

  Naganuma, Kenji ^a   Kawashima, Takayuki ^a   Okazaki, Renji ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN WOMEN'S UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033235051     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.1139     Document Type: Article

References (18)

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14. 2O-), was developed by Martin for stabilizing hypervalent species: E. F. Perozzi, R. S. Michalak, G. D. Figuly, W. H. Stevenson III, W. H. Dess, M. R. Ross, and J. C. Martin, J. Org. Chem., 46, 1049 (1981).
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16. 5: C, 43.54; H, 3.65; N, 3.50%.
17. 3 solution of 1a with 100 equiv. of acetic acid at room temperature. See Ref 3.
18. The thermolysis of pentacoordinate 1,2-oxasiletanides bearing a n-propyl group, which is not as bulky as neopentyl group, at the 3-position in the presence of acetic acid (10 equiv.) gave the corresponding olefin (94%) and alcohol (6%). This result clearly indicates that the steric factor is important for the determination of the reaction modes.