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Volumn 37, Issue 7, 2008, Pages 740-741

Manganese-catalyzed synthesis of hydantoin derivatives from terminal alkynes and isocyanates

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EID: 49149100728 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2008.740 Document Type: Article

Times cited : (38)

References (29)

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24
- 49149118283
- The structure of 3a was determined by a comparison with the reported data in ref 6a, and by X-ray single-crystal structure analysis.
- The structure of 3a was determined by a comparison with the reported data in ref 6a, and by X-ray single-crystal structure analysis.

25
- 49149103488
- Investigation of temperature in the reaction between phenyl-acetylene (1a) (1.0 equiv) and p-methoxyphenyl isocyanate (2b) (2.0 equiv): 5o°C, 0%; 80°C, 30%; 100°C, 45%; 115°C, 59%; 135°C, 62%; 15o°C, 75%.
- Investigation of temperature in the reaction between phenyl-acetylene (1a) (1.0 equiv) and p-methoxyphenyl isocyanate (2b) (2.0 equiv): 5o°C, 0%; 80°C, 30%; 100°C, 45%; 115°C, 59%; 135°C, 62%; 15o°C, 75%.

26
- 49149103758
- An iron complex, Fe(acac)3 (5.0mol, provided hydantoin derivative 3a in 8% yield. Only a trace amount of hydantoin 3a was obtained in the presence of a ruthenium complex, Ru3(CO) 12 or RuH2(CO)(PPh3)3. The reaction did not proceed using ReBr(CO)5, ReBr(CO)3thf, 2, FeCl3, and RhCl3
- 3.

27
- 49149090525
- In a reported paper (ref 6, the formation reaction of hydantoins proceeded stoichiometrically using an iron complex, Fe(CO)5. However, as a result of our investigation, the iron complex promoted the reaction catalytically
- 5. However, as a result of our investigation, the iron complex promoted the reaction catalytically.

28
- 49149089792
- Another reaction mechanism can be considered: (1) the formation of a manganese-alkylidene intermediate; (2) nucleophilic addition of isocyanate to the intermediate; (3) addition of another isocyanate; (4) addition of a manganese-carbon bond of the alkenylmanganese moiety; (5) isomerization of an olefinic moiety
- Another reaction mechanism can be considered: (1) the formation of a manganese-alkylidene intermediate; (2) nucleophilic addition of isocyanate to the intermediate; (3) addition of another isocyanate; (4) addition of a manganese-carbon bond of the alkenylmanganese moiety; (5) isomerization of an olefinic moiety.

29
- 49149101674
- Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
- Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.

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