TY - JOUR
T1 - Catalytic preparation of aziridines with an iron lewis acid
AU - Mayer, Michael F.
AU - Mahmun Hossain, M.
PY - 1998/10/2
Y1 - 1998/10/2
N2 - The iron Lewis acid, [(;75-C5H5)Fe(CO)2(THF)]+[BF4]-) was found to be an effective catalyst for the preparation of aziridines. This new method provides a facile, one-step route to predominantly cisaziridines, with yields up to 95%, from compounds with a diazo functionality and a variety of substituted AT-benzylidene imines with N-aryl or AT-alkyl groups. The reaction mechanism is believed to proceed through an electrophilic iminium ion intermediate. To support this idea, the iron Lewis acid-imine complex [(?75-C5H5)Fe(CO)2(PhCH=NPh)]+[BF.j]- was prepared, characterized, and reacted with different diazo compounds to provide the resultant czs-aziridines. Alternatively, it may be possible that the aziridines were derived from an electrophilic carbenoid intermediate, as is often proposed. Thus, the iron carbene [(2-CsIWFeCCOMCHPhOl+LSOaCFg]- was prepared and treated with AT-benzylideneaniline; however, the resultant aziridine was not formed.
AB - The iron Lewis acid, [(;75-C5H5)Fe(CO)2(THF)]+[BF4]-) was found to be an effective catalyst for the preparation of aziridines. This new method provides a facile, one-step route to predominantly cisaziridines, with yields up to 95%, from compounds with a diazo functionality and a variety of substituted AT-benzylidene imines with N-aryl or AT-alkyl groups. The reaction mechanism is believed to proceed through an electrophilic iminium ion intermediate. To support this idea, the iron Lewis acid-imine complex [(?75-C5H5)Fe(CO)2(PhCH=NPh)]+[BF.j]- was prepared, characterized, and reacted with different diazo compounds to provide the resultant czs-aziridines. Alternatively, it may be possible that the aziridines were derived from an electrophilic carbenoid intermediate, as is often proposed. Thus, the iron carbene [(2-CsIWFeCCOMCHPhOl+LSOaCFg]- was prepared and treated with AT-benzylideneaniline; however, the resultant aziridine was not formed.
UR - http://www.scopus.com/inward/record.url?scp=0000513097&partnerID=8YFLogxK
U2 - 10.1021/jo9804792
DO - 10.1021/jo9804792
M3 - Article
AN - SCOPUS:0000513097
SN - 0022-3263
VL - 63
SP - 6839
EP - 6844
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 20
ER -