2013
DOI: 10.1039/c3ra43307b
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PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene

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Cited by 18 publications
(11 citation statements)
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“…Our synthetic strategy is shown in Scheme 1. MeO-gDCC containing 1 was prepared from the selective cyclopropanation of the electron-rich alkene of commercially available 1methoxyl-1,4-cyclohexadiene using a protocol 32 that avoids the tedious workup involved with conventional phase transfer agents (e.g., tetrabutylammonium salts). Subsequent ozonolysis and reduction produces diol 2 as a colorless oil.…”
mentioning
confidence: 99%
“…Our synthetic strategy is shown in Scheme 1. MeO-gDCC containing 1 was prepared from the selective cyclopropanation of the electron-rich alkene of commercially available 1methoxyl-1,4-cyclohexadiene using a protocol 32 that avoids the tedious workup involved with conventional phase transfer agents (e.g., tetrabutylammonium salts). Subsequent ozonolysis and reduction produces diol 2 as a colorless oil.…”
mentioning
confidence: 99%
“…Subsequently, [HMTH] 2 H 2 [SiW 12 O 40 ] (3 mol %) was applied as catalyst for the optimization of different green solvents including polyethylene glycols, i.e., PEG200 and PEG400, cyclopentyl methyl ether (CPME), dimethyl carbonate (DMC), ethylene carbonate (EC), propylene carbonate (PC). As can be seen in Figure A, only 1% and 2% yields were observed when the reaction was conducted in PEG200 and PEG400, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…Commercially available 2-iodopropane ( 2a ), cyclohexyl iodide ( 2b ), and 1,1,1-trifluoro-3-iodopropane ( 2c ) were distilled prior to use. Reagents shown below were synthesized according to literature procedures: N -methyl-1-phenylmethanimine ( 1a ), N -(2-methoxyethyl)-1-phenylmethanimine ( 1b ), 1-(3-methoxyphenyl)- N -methylmethanimine ( 1c ), methyl 2-(benzylideneamino)­acetate ( 1d ), 2-(benzylideneamino)- N , N -dimethylethan-1-amine ( 1e ), N ,1-diphenylmethanimine ( 1f ), N -allyl-1-phenylmethanimine ( 1g ), N -benzyl-1-phenylmethanimine ( 1h ), N -cyclopropyl-1-phenylmethanimine ( 1i ), 1-(4-chlorophenyl)- N -phenylmethanimine ( 4a ), 1-(4-methoxyphenyl)- N -phenylmethanimine ( 4b ), N -(4-bromophenyl)-1-phenylmethanimine ( 4c ), 1-(4-methoxyphenyl)- N -(p-tolyl)­methanimine ( 4d ), N ,1-bis­(4-methoxyphenyl)­methanimine ( 4e ), 1-(furan-2-yl)- N -(4-methoxyphenyl)­methanimine ( 4f ), N -benzylidene-4-methylbenzenesulfonamide ( 6 ), tert -butyl 4-iodopiperidine-1-carboxylate ( 2d ), (3-iodobutyl)­benzene ( 2e ), (3-iodopropyl)­benzene ( 2f ), 4-iodobut-1-ene ( 2g ), ethyl 4-iodobutanoate ( 2h ), 4-iodobutanenitrile ( 2i ), (iodomethyl)­trimethylsilane ( 2j ), 4-iodobutyl pivalate ( 2k ), iodocyclooctane ( 2f ), 1-iodo-2-methylpropane ( 2m ), 5-iodopent-1-ene ( 2n ), 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate ( 8 ), 2,4,6-tris­(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) …”
Section: Methodsmentioning
confidence: 99%