The comparative nucleophilicity of naphthoxide derivatives in reactions with a fast-red TR dye: A discovery-oriented capstone project for the second-year organic laboratory

Journal of Chemical Education

Volumn 85, Issue 9, 2008, Pages 1271-1273

  Mascarenhas, Cheryl M ^a  

^a BENEDICTINE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 51249091199     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed085p1271     Document Type: Article

References (11)

1. For an undergraduate experiment using azo dyes, see: Gung. B. W.; Taylor, R. T. J. Chem. Educ. 2004, 81, 1630-1632.
2. Lavastre, O.; Morken, J. P. Angew. Chem., Int. Ed. 1999, 38, 3163-3165.
3. Townes, J. A.; Evans, M. A.; Queffelec, J.; Taylor, S.J.; Morken, J. P. Organic Lett. 2002, 4, 2537-2540.
4. a Tanaka, F.; Kerwin, L.; Kubitz, D.; Lerner, R. A.; Barbas C. F., III. Bioorg. Med. Chem. Lett. 2001, 11, 2983-2986.
5. b Boga, C.; Degani,J.; Del Vecchio, E.; Fochi, R.; Forlani, L.; Todesco, P. E. Eur. J. Org. Chem. 2002, 3837-3843.
6. For a discussion of hydrogen-bonding contributing to ortho diazotization of naphthol derivatives, see: Zollinger, H. Diazo Chemistry I: Aromatic and Heteroaromatic Compound; VCH: Weinheim, Germany, 1994; pp 307-308.
7. For general acetate hydrolyses under basic conditions, see: a Paredes, R.; Gil, J.; Ocampo, P. J. Chem. Educ. 1988, 65, 1109-1110.
8. b Bender, M. L; Turnquest, B. W. J. Am. Chem. Soc. 1957, 79, 1656-1662.
9. For examples of ester hydrolyses in the chemical educational literature, see: (a) Lombardo, A. J. Chem. Educ. 1982, 59, 887-888.
10. (b) Hadd, A. G.; Lehmpuhl, D. W.; Kuck, L R.; Birks, J. W. J. Chem. Educ. 1999, 76, 1237-1240.
11. (c) Bugg, T. D. H.: Lewin, A. M.; Catlin, E. R. J. Chem. Educ. 1997, 74, 105-107.