Diiodosilane: A reagent for mild, efficient conversion of carbamates to ureas via isocyanates

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3239-3240

  Gastaldi, Stéphane ^a   Weinreb, Steven M ^b   Stien, Didier ^c  

^a AIX MARSEILLE UNIVERSITY   (France)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

^c UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; DIIODOSILANE; ISOCYANATE; REAGENT; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION KINETICS; CHLORINATION; INFRARED SPECTROSCOPY; LOW TEMPERATURE PROCEDURES; NONHUMAN; NOTE; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0034685972     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9919714     Document Type: Note

References (13)

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8. Chong, P. Y.; Janicki, S. Z.; Petillo, P. A. J. Org. Chem. 1998, 63, 8515 and references cited.
9. For other synthetic uses of this silane, see: Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995; Vol. 3, p 1905.
10. For a review on synthesis of ureas, see: Petersen, U. Methoden Org. Chem. (Houben-Weyl) 1983, E4, 334.
11. It should be noted that iodotrimethylsilane cleaves Boc carbamates to amines: Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543.
12. It should be noted that iodotrimethylsilane cleaves Boc carbamates to amines: Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543.
13. It should be noted that iodotrimethylsilane cleaves Boc carbamates to amines: Jung, M. E.; Lyster, M. A. J. Chem. Soc., Chem. Commun. 1978, 315. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543.