N-Fluorination of trans-3-trifluoromethyl-2-methoxycarbonyl (6) with elemental fluorine (F-2/NaF, freon 113, at -5 degrees C), stereoselectively affords the trans-N-fluoro derivative (F-N relative to COOCH3), fluorination occurring from the side shielded by the CF3 group. Chlorination of 6 and its amide 7 with Bu'OCl (CH2Cl2 at -5 and -80 degrees C) still affords the trans-N-chloroderivatives, though to a lesser extent (50% and 15%, respectively). The stereocontrol of the reaction seems to be due to the intramolecular H-bond.
Synthesis and stereodirected N-halogenation of trans-3-trifluoromethyl-2-methoxycarbonylaziridine / Prati, Fabio; Forni, Arrigo; Moretti, Irene; Torre, Giovanni; Vv, Rozhkov; Kn, Makarov; Ii, Chervin; Rg, Kostyanovsky. - In: JOURNAL OF FLUORINE CHEMISTRY. - ISSN 0022-1139. - STAMPA. - 89:(1998), pp. 177-181.
Synthesis and stereodirected N-halogenation of trans-3-trifluoromethyl-2-methoxycarbonylaziridine
PRATI, Fabio;FORNI, Arrigo;MORETTI, Irene;TORRE, Giovanni;
1998
Abstract
N-Fluorination of trans-3-trifluoromethyl-2-methoxycarbonyl (6) with elemental fluorine (F-2/NaF, freon 113, at -5 degrees C), stereoselectively affords the trans-N-fluoro derivative (F-N relative to COOCH3), fluorination occurring from the side shielded by the CF3 group. Chlorination of 6 and its amide 7 with Bu'OCl (CH2Cl2 at -5 and -80 degrees C) still affords the trans-N-chloroderivatives, though to a lesser extent (50% and 15%, respectively). The stereocontrol of the reaction seems to be due to the intramolecular H-bond.
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