42136-65-2Relevant academic research and scientific papers
Synthesis and reaction of 1-azabicyclo[3.1.0]hexane
Hayashi, Kazuhiko,Kujime, Eiko,Katayama, Hajime,Sano, Shigeki,Shiro, Motoo,Nagao, Yoshimitsu
experimental part, p. 1142 - 1146 (2010/03/31)
The effective formation of 1-azabicyclo[3.1.0]hexane (5) by treatment of 2-(bromomethyl)pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on int
Catalytic preparation of aziridines with an iron lewis acid
Mayer, Michael F.,Mahmun Hossain
, p. 6839 - 6844 (2007/10/03)
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.
ONE POT SYNTHESIS OF HOMOCHIRAL AZIRIDINES AND AMINOALCOHOLS FROM HOMOCHIRAL 1,2-CYCLIC SULFATES
Lohray, B. Bhushan,Gao, Yun,Sharpless, K. Barry
, p. 2623 - 2626 (2007/10/02)
Preparations of homochiral N-substituted aziridines and aminoalcohols from 1,2-cyclic sulfates are reported.Primary amines react with cyclic sulfates to give β-aminosulfates which can be converted either to aziridines or to aminoalcohols by treatment with
Base-induced Reactions of N-Substituted Dibenzylamine N-Oxides and Related Compounds: A Novel Aziridine Forming Reaction
Takayama, Hiroaki,Nomoto, Takashi
, p. 408 - 409 (2007/10/02)
The reactions of the N-substituted dibenzylamine N-oxides (1) (R = benzyl, n-butyl, or cyclohexyl) with n-butyl-lithium in ether gave the corresponding cis-2,3-diphenylaziridines in moderate yields (20-42percent); application of this reaction to other related compounds enabled a novel ring system, 10,11-dihydro-10,11,5-nitrilomethanodibenzocycloheptene to be synthesized.
CYCLOADDITIONS OF 1-SUBSTITUTED CIS- AND TRANS-2,3-DIPHENYLAZIRIDINES VIA AZOMETHINE YLIDES
Huisgen, Rolf,Matsumoto, Kiyoshi,Ross, Carl Heinz
, p. 1131 - 1136 (2007/10/02)
1-Benzyl-cis- and -trans-2,3-diphenylaziridines combine at 110 deg C with olefinic dipolarophiles to produce pyrrolidine derivatives in high yields.Stereospecific conrotation for the ring opening of the aziridines to azomethine ylides was deduced from the structure of the cycloadducts.The rate contstants of adduct formation with diethyl fumarate do not depend on the concentration of the dipolarophile.In contrast, ethyl cis- and trans-2,3-diphenylaziridine-1-carboxylate produce with dimethyl fumarate at 145 deg C the same mixture of diastereomeric pyrrolidines both of which are derived from the exo, endo- diphenyl substituted azomethine ylide.
