Novel regiochemistry in the aqueous singlet oxygen ene reactions of carboxylic acid salts: A comparison of substrate structure

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 715-718

  Stensaas, Kristina L ^a   Bajaj, Anisha ^a   Al Turk, Akram ^a  

^a MILLSAPS COLLEGE   (United States)

Author keywords

Aqueous solvent; Ene reactions; Hydrogen bonding; Singlet oxygen

Indexed keywords

2,3 DIMETHYL 2 BUTENOIC ACID SALT; 3 ETHOXYCARBONYL 5,6 DIHYDRO 2 METHYL 4H PYRANE ACID SALT; 3 HEXENOID ACID SALT; ANGELIC ACID SALT; CARBOXYLIC ACID SALT; DEUTERIUM OXIDE; OXIDE; SOLVENT; TIGLIC ACID SALT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; QUANTITATIVE ANALYSIS; STRUCTURE ANALYSIS;

EID: 11144261495     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.173     Document Type: Article

References (17)

1. Schenck, G.O. Patent DE-B 933925, 1943
2. G.O. Schenck, H. Eggert, and W. Denk Liebigs Ann. Chem. 584 1953 177 198
3. D.A. Singleton, C. Hang, M.J. Szymanski, M.P. Meyer, A.G. Leach, K.T. Kuwata, J.S. Chen, A. Greer, C.S. Foote, and K.N. Houk J. Am. Chem. Soc. 125 2003 1319 1328
4. A.A. Frimer, and L.M. Stephenson A.A. Frimer The Singlet Oxygen Ene Reaction Vol. 2 1985 CRC Boca Raton, Fl 67 91 Two recent reviews include:
5. E.L. Clennan Tetrahedron 56 2000 9151
6. M. Stratakis, and M. Orfanopoulos Tetrahedron 56 2000 1595 1615
7. Y. Elemes, and C.S. Foote J. Am. Chem. Soc. 114 1992 6044 6049
8. L.M. Stephenson, M.B. Grdina, and M. Orfanopoulos Acc. Chem. Res. 13 1980 419 425
9. K.L. Stensaas, J.A. Payne, A.N. Ivancic, and A. Bajaj Tetrahedron Lett. 43 2002 25 27
10. Salts 1, 2, and 3 were synthesized from their corresponding acids using equivalent amounts of sodium hydroxide. The acid of 3 was synthesized using the Reformatsky reaction (Huston, R. C.; Goerner, G. L. J. Am. Chem. Soc. 1940, 62, 576). Compound 4 was prepared by saponification of its corresponding ethyl ester
11. M. Orfanopoulos, and M. Stratikis Tetrahedron Lett. 32 49 1991 7321 7324
12. M. Orfanopoulos, M.B. Grdina, and L.M. Stephenson J. Am. Chem. Soc. 101 1979 275 276
13. Jeffrey, G. A. Introduction to Hydrogen Bonding; New York, 1997; p 46
14. S. Inagaki, H. Fujimoto, and K. Fukui Chem. Lett. 1976 749
15. D. Lerdal, and C.S. Foote Tetrahedron Lett. 35 1978 3227 3230
16. The ratio of 64/36 for cis-3-hexenoic acid was previously reported in Ref. 12
17. M. Stratikis, and M. Orfanopoulos Tetrahedron Lett. 38 6 1997 1067 1070