5-methoxyfuroxano[3,4-d]pyrimidine: A highly reactive neutral electrophile

Journal of Physical Organic Chemistry

Volumn 16, Issue 8, 2003, Pages 431-437

  Remennikov, Grigoriy Ya ^a   Kempf, Bernhard ^a   Ofial, Armin R ^a   Polborn, Kurt ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

adducts; Furoxanopyrimidine; Kinetics; Linear free energy relationship; Nucleophilic addition

Indexed keywords

COMPUTATIONAL COMPLEXITY; CORRELATION METHODS; FREE ENERGY; REACTION KINETICS; SUBSTITUTION REACTIONS;

ELECTROPHILES;

AROMATIC HYDROCARBONS;

EID: 0042364933     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.606     Document Type: Conference Paper

References (26)

1. (a) Terrier F. Chem. Rev. 1982; 82: 77-152
2. (b) Illuminati G, Siegel F. Adv. Heterocycl. Chem. 1983; 34: 305-444
3. (c) Buncel E, Dust JM, Terrier F. Chem. Rev. 1995; 95: 2261-2280.
4. Terrier F, Kizilian E, Halle JC, Buncel E. J. Am. Chem. Soc. 1992; 114: 1740-1742.
5. (a) Terrier F, Goumont R, Pouet MJ, Halle JC. J. Chem. Soc., Perkin Trans. 2 1995; 1629-1637
6. (b) Buncel E, Renfrow RA, Strauss MJ. J. Org. Chem. 1987; 52: 488-495.
7. Ghosh PB, Ternai B, Whitehouse MW. Med. Res. Rev. 1981; 1: 159-187.
8. (a) Sheremetev AB. Russ. Chem Rev. 1999; 68: 137-148; Usp. Khim. 1999; 68: 154-166
9. (a) Sheremetev AB. Russ. Chem Rev. 1999; 68: 137-148; Usp. Khim. 1999; 68: 154-166
10. (b) Sako M, Oda S, Ohara S, Hirota K, Maki Y. J. Org. Chem. 1998; 63: 6947-6951
11. (c) Remennikov GYa. Chem. Heterocycl. Compd. 1997; 33: 1369-1381; Khim. Geterotsikl. Soedin. 1997; 33: 1587-1602.
12. (c) Remennikov GYa. Chem. Heterocycl. Compd. 1997; 33: 1369-1381; Khim. Geterotsikl. Soedin. 1997; 33: 1587-1602.
13. Terrier F, Sebban M, Goumont R, Halle JC, Moutiers G, Cangelosi I, Buncel E. J. Org. Chem. 2000; 65: 7391-7398.
14. Remennikov GYa, Pirozhenko VV, Dyachenko IA. Khim. Geterotsikl. Soedin. 1992; 101-106.
15. Remennikov GYa, Pirozhenko VV, Vdovenko SI, Kravchenko SA. Chem. Heterocycl. Compd. 1998; 34: 104-110; Khim. Geterotsikl. Soedin. 1998; 34: 112-119.
16. Remennikov GYa, Pirozhenko VV, Vdovenko SI, Kravchenko SA. Chem. Heterocycl. Compd. 1998; 34: 104-110; Khim. Geterotsikl. Soedin. 1998; 34: 112-119.
17. Mayr H, Patz M. Angew. Chem. 1994; 106: 990-1010; Angew. Chem., Int. Ed. Engl. 1994; 33: 938-957.
18. Mayr H, Patz M. Angew. Chem. 1994; 106: 990-1010; Angew. Chem., Int. Ed. Engl. 1994; 33: 938-957.
19. Mayr H, Patz M, Gotta MF, Ofial AR. Pure Appl. Chem. 1998; 70: 1993-2000.
20. Mayr H, Kuhn O, Gotta MF, Patz M. J. Phys. Org. Chem. 1998; 11: 642-654.
21. Mayr H, Kempf B, Ofial AR. Acc. Chem. Res. 2003; 36: 66-77.
22. Mayr H, Bug T, Gotta MF, Hering N, Irrgang B, Janker B, Kempf B, Loos R, Ofial AR, Remennikov G, Schimmel H. J. Am. Chem. Soc. 2001; 123: 9500-9512.
23. Khmel'nitski LI, Novikov SS, Godovikova TI. Chemistry of Furoxans (Reactions and Application). Nauka: Moscow, 1983; 62 (in Russian).
24. Steiner G, Huisgen R. J. Am. Chem. Soc. 1973; 95: 5056-5058.
25. Reichardt C. Solvents and Solvent Effects in Organic Chemistry (2nd edn). VCH: Weinheim, 1988; 147.
26. Brown DJ, Sugimoto T. J. Chem. Soc. C 1970; 2661-2666.