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Volumn 10, Issue 3, 2013, Pages 195-198

A novel synthesis of 1,4,7,10-tetraazacyclododecane by the tandem reaction of a vinylsulfonium salt

Author keywords

1,4,7,10 Tetraazacyclododecane; MRI; Tandem Reaction; Vinylsulfonium

Indexed keywords


EID: 84879806547     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178611310030009     Document Type: Article
Times cited : (5)

References (31)
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    • A possible mechanism for this cycliaztion was that the aminal nitrogen acted as a nucleophile to attack the highly electrophilic vinylsulfonium species and produced the sulfonium ylid species. After being protonated, the ylid species would be converted into an alkylsulfonium species, which would be subsequently attacked by the gem nitrogen in a nucleophilic manner, and extruded the diphenylsulfide as a by product. Similar proposals could be found in Ref. [11b] and [11c]
    • A possible mechanism for this cycliaztion was that the aminal nitrogen acted as a nucleophile to attack the highly electrophilic vinylsulfonium species and produced the sulfonium ylid species. After being protonated, the ylid species would be converted into an alkylsulfonium species, which would be subsequently attacked by the gem nitrogen in a nucleophilic manner, and extruded the diphenylsulfide as a by product. Similar proposals could be found in Ref. [11b] and [11c].
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    • This procedure is supposed to proceed through the formation of a bisamidinium salt intermediate, which will be hydrolyzed under alkaline condions to provide the final cyclen
    • This procedure is supposed to proceed through the formation of a bisamidinium salt intermediate, which will be hydrolyzed under alkaline condions to provide the final cyclen.
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