Summary.
It is demonstrated that electron-rich disubstituted acetophenones react according to various electrophilic nitration conditions that generally lead to ipso substitution accompanying the conventional reaction. The hydroxy substituent does not seem prone to favor such behaviour.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Nightingale DV (1947) Chem Rev, 117
RB Moodie K Schofield (1976) Acc Chem Res 9 287 Occurrence Handle10.1021/ar50104a002
JG Traynham (1983) J Chem Educ 60 937
A Fischer GN Henderson S Raymahasay (1987) Can J Chem 65 1233
RG Clewley A Fischer GN Henderson (1989) Can J Chem 67 1472
(a) Coombes RG, Golding JG, Hadjigeorgiou P (1979) J Chem Soc Perkin Trans 2, 1451; (b) Tashiro M, Yamato T, Fukata G, Fukuda Y (1981) J Org Chem 46: 2376; (c) Yamato T, Kamimura H, Tsuzuki H (1998) Can J Chem 76: 997
(a) Lancelot J-C, Letois B, Rault S, Huy Dung N, Saturnino C, Robba M (1991) Gazz Chim Ital 121: 301; (b) Einhorn J, Halut-Desportes S, Demerseman P, Royer R (1983) J Chem Res (S) 98
(a) Comins DL, Myoung YC (1990) J Org Chem 55: 292; (b) Barrett AG, Dauzonne D, O’Neil IA, Renaud A (1984) J Org Chem 49: 4409
(a) Wilbur DS, Stone WE, Anderson KW (1983) J Org Chem 48: 1542; (b) Coe PL, Stuart AM, Moody DJ (1998) J Fluorine Chem 92: 27
SR Hartshorn (1974) Chem Soc Rev 3 167 Occurrence Handle10.1039/cs9740300167
WB Motherwell S Vázquez (2000) Tetrahedron Lett 41 9667 Occurrence Handle10.1016/S0040-4039(00)01746-9
P Cotelle J-P Catteau (1996) Synth Commun 26 4105
VJ Harding (1912) J Chem Soc, Abstract 99 1585
For example: (a) Catoen-Chackal S, Facompré M, Houssin R, Pommery N, Goossens J-F, Colson P, Bailly C, Hénichart J-P (2004) J Med Chem 47: 3665; (b) Perzyna A, Klupsch F, Houssin R, Pommery N, Lemoine A, Hénichart J-P (2004) Bioorg Med Chem Lett 14: 2363; (c) Malecki N, Carato P, Rigo B, Goossens J-F, Houssin R, Bailly C, Hénichart J-P (2004) Bioorg Med Chem 12: 641; (d) Perzyna A, Houssin R, Barbry D, Hénichart J-P (2002) Synlett, 2077; (e) Chackal S, Houssin R, Hénichart J-P (2002) J Org Chem 67: 3502; (f) Perzyna A, Marty C, Facompré M, Goossens J-F, Pommery N, Colson P, Houssier C, Houssin R, Hénichart J-P, Bailly C (2002) J Med Chem 45: 5809; (g) Goossens J-F, Bouey-Bencteux E, Houssin R, Hénichart J-P, Colson P, Houssier C, Laine W, Baldeyrou B, Bailly C (2001) Biochemistry 40: 4663
H Aichaoui D Lesieur J-P Hénichart (1992) J Heterocycl Chem 29 171
Z Moussavi P Depreux D Lesieur N Cotelle J Sauzières M-O Plancke J-C Fruchart (1991) Farmaco 46 339 Occurrence Handle1859587
DE Thurston DS Bose AS Thompson PW Howard A Leoni SJ Croker TC Jenkins S Neidle JA Hartley LH Hurley (1996) J Org Chem 61 8141 Occurrence Handle10.1021/jo951631s Occurrence Handle11667802
P Laszlo A Cornélis (1988) Aldrichimica Acta 21 97
RL Clark AA Pessolano (1958) J Am Chem Soc 80 1662 Occurrence Handle10.1021/ja01540a038
G Wagner S Leistner (1971) Pharmazie 26 280 Occurrence Handle5563058
MT Le Bris (1984) J Heterocycl Chem 21 551
J Marquet M Moreno-Mañas A Vallribera A Virgili J Bertran A Gonzalez-Lafont JM Lluch (1987) Tetrahedron 43 351 Occurrence Handle10.1016/S0040-4020(01)89963-4
GA Olah SJ Kuhn SH Flood JC Evans (1962) J Am Chem Soc 84 3687 Occurrence Handle10.1021/ja00878a019
JP Hénichart JL Bernier C Vaccher R Houssin V Warin F Baert (1980) Tetrahedron 36 3535 Occurrence Handle10.1016/0040-4020(80)88049-5
JP Bonte D Lesieur JC Cazin M Cazin C Lespagnol (1974) Eur J Med Chem 9 497
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Malecki, N., Carato, P., Houssin, R. et al. Electrophilic Nitration of Electron-Rich Acetophenones. Monatsh. Chem. 136, 1601–1606 (2005). https://doi.org/10.1007/s00706-005-0346-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-005-0346-3