61213-19-2Relevant academic research and scientific papers
Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams
Iwamatsu, Sho-ichi,Kondo, Hideo,Matsubara, Kouki,Nagashima, Hideo
, p. 1687 - 1706 (1999)
Treatment of α,α,γ-trichlorinated γ-lactams with a catalytic amount of CuCl(bipyridine) complex resulted in facile activation of their carbon- chlorine bond at the α-position. Addition of the carbon moiety and the chlorine atom to olefins furnished the carbon-carbon bond forming reaction at the α-position of the carbonyl group. In certain trichlorinated γ-lactams including a carbon-carbon double bond at an appropriate position, intramolecular addition reactions took place to give bicyclic lactams. Sequential reactions consisting of the cyclization of N-allyl trichloroacetamides followed by the inter- or intramolecular carbon-carbon bond forming reactions at the α-position of the lactams were also achieved. Efficiency of the catalyst and reaction rate was dependent on the protecting group of the nitrogen atom of the γ-lactams; N-tosyl derivatives gave better results than the corresponding N-benzyl homologues. The molecular structure of the representative products revealed the stereochemical outcome of the reactions.
Olefin cyclopropanations via sequential atom transfer radical addition-dechlorination reactions
Thommes, Katrin,Severin, Kay
experimental part, p. 188 - 190 (2011/07/07)
In organic synthesis, cyclopropanation reactions are often performed with Simmons-Smith-type reagents or by transition metal catalyzed reactions of olefins with diazo compounds. A novel method for the synthesis of substituted cyclopropanes is described that is based on a two-step reaction sequence. Olefins are reacted with 1,1'-dichlorides in a Ru-catalyzed atom transfer radical addition (ATRA) process and the resulting 1,3-dichlorides are directly converted into cyclopropanes by reductive coupling with magnesium. This one-pot procedure is applicable to a variety of substrates and can be performed in an inter- or intramolecular fashion. Schweizerische Chemische Gesellschaft.
Transition Metal-Catalyzed Radical Cyclizations: A Low-Temperature Process for the Cyclization of N-Protected N-Allyltrichloroacetamides to Trichlorinated γ-Lactams and Application to the Stereoselective Preparation of β,γ-Disubstituted γ-Lactams
Nagashima, Hideo,Ozaki, Nobuyasu,Ishii, Masayuki,Seki, Koji,Washiyama, Masayoshi,Itoh, Kenji
, p. 464 - 470 (2007/10/02)
Cyclisations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding β,γ-trichlorinated γ-lactams in high yields.The reactions proceed at temperatures from -78 deg C to room temperature.Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the γ-lactams formed were dependent on the substituents on the nitrogen atom.The stereochemical outcome is compared with that of free-radical cyclization.
Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides
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, (2008/06/13)
Acyclic and alicyclic N-substituted halo-2-pyrrolidinones having the formula STR1 in which Q is oxygen or sulfur; R is lower alkyl, haloalkyl, alkenyl, cycloalkyl, cycloalkylalkyl, benzyl and chlorobenzyl; X is hydrogen or chlorine, Y is chlorine or bromine and Z is chlorine or bromine, provided that when R is allyl, Y and Z are each chlorine or bromine, and provided that when R is cyclohexyl, X is other than chlorine. The compounds of this invention are prepared by a novel process and are useful as herbicides.
Preparation of acyclic and alicyclic N-substituted halo-2-pyrrolidinones
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, (2008/06/13)
Acyclic and alicyclic N-substituted halo-2-pyrrolidinones having the formula STR1 in which Q is oxygen or sulfur; R is lower alkyl, haloalkyl, alkenyl, cycloalkyl, cycloalkylalkyl, benzyl and chlorobenzyl; X is hydrogen or chlorine, Y is chlorine or bromine and Z is chlorine or bromine, provided that when R is allyl, Y and Z are each chlorine or bromine, and provided that when R is cyclohexyl, X is other than chlorine. The compounds of this invention are prepared by a novel process and are useful as herbicides.
