F. Prati, A. Forni, I. Moretti
May 29, 1998
Citations
0
Influential Citations
5
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract N -Fluorination of trans -3-trifluoromethyl-2-methoxycarbonylaziridine (6) with elemental fluorine (F 2 /NaF,freon 113,at −5 °C), ster-eoselectively affords the trans - N -fluoro derivative (F-N relative to COOCH 3 ),fluorination occurring from the side shielded by the CF 3 group. Chlorination of 6 and its amide 7 with Bu'OCl (CH 2 Cl 2 at −5 and −80 °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.