Mechanistic aspects of the substrate ionization step in aminium salt catalyzed cyclopropanation

Research on Chemical Intermediates

Volumn 23, Issue 1, 1997, Pages 1-16

  Yueh, W ^a   Bauld, N L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038222508     PISSN: 09226168     EISSN: None     Source Type: Journal    
DOI: 10.1163/156856797X00349     Document Type: Article

References (9)

1. R.I. Walter, J. Am. Chem. Soc 77, 5999, 1955.
2. W. Schmidt and E. Steckhan, Chem Ber 113, 577 (1980).
3. G. Stufflebeme, K.T. Lorenz, and N.L. Bauld, J Am Chem. Soc. 108, 4234 (1986).
4. W. Yueh and N.L. Bauld, J. Am. Chem Soc. 117, 5671 (1995).
5. The oxidation potentials of stilbene and ethyl diazoacetate are 1.59 and ≥ 2.1 V versus SCE, respectively.
6. The oxidation potentials of representative cyclopropanated products are, respectively: 5b, 1.624; 5c, 1.728; 5f, 1.960 V versus SCE.
7. The oxidation potentials of the corresponding Diels-Alder adducts derived from 3b, 3c, and 3f are, respectively. 1.452, 1.456, and 1.456 V versus SCE.
8. W. Yueh and N.L. Bauld, J. Am. Chem. Soc (1995), submitted for publication.
9. +• have a ρ value which is significantly lowered by a chain mechanistic component.