Selenium-assisted one-pot synthesis of carbodiimides from isocyanides and primary amines

Synlett

Volumn , Issue 1, 1999, Pages 75-76

  Fujiwara, Shin Ichi ^a   Matsuya, Takahiro ^b   Maeda, Hajime ^b,d   Shin Ike, Tsutomu ^a   Kambe, Nobuaki ^b   Sonoda, Noboru ^c  

^a OSAKA DENTAL UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c KANSAI UNIVERSITY   (Japan)

^d Osaka Prefecture University   (Japan)

Author keywords

Carbodiimide; Isocyanide; Selenium; Selenourea

Indexed keywords

AMINE; CYANAMIDE; CYANIDE; SELENIUM;

ARTICLE; COUPLING FACTOR; DRUG ISOLATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0032956042     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2559     Document Type: Article

References (16)

1. Reviews for synthesis, properties, and reactions of carbodiimides: (a) Muthyala, R. In Comprehensive Organic Functional Group Transformations, Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Pergamon Press: Oxford, 1995; Vol. 5, pp 1061-1089.
2. (b) Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589-636.
3. (c) Wagner, K.; Findeisen, K.; Schaefer, W.; Dietrich, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 819-830.
4. (d) Mikolajczyk, M; Kielbasinski, P. Tetrahedron 1981, 37, 233-284.
5. (e) Kurzer, F.; Douraghi-Zadeh, K. Chem. Rev. 1967, 67, 107-152.
6. Sonoda, N.; Yamamoto, G.; Tsutsumi, S. Bull. Chem. Soc. Jpn. 1972, 45, 2937-2938.
7. 1H FT NMR Spectra, Vol. 1, 1993, 1413B and 1413A, respectively.
8. 3) δ 31.5, 57.3, 122.9, 124.3, 129.0, 135.9, 140.6.
9. N-Butyl-N'-tert-butylthìourea was prepared by the reaction of tert-butylisothiocyanate with butylamine: Nair, G. V. Indian J. Chem. 1966, 4, 516-520; Chem. Abstr. 1967, 67, 11290.
10. N-Butyl-N'-tert-butylthìourea was prepared by the reaction of tert-butylisothiocyanate with butylamine: Nair, G. V. Indian J. Chem. 1966, 4, 516-520; Chem. Abstr. 1967, 67, 11290.
11. One-pot synthesis of carbodiimides from isocyanides and amines by the use of transition metal complexes, see: (a) Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1975, 40, 2981-2982.
12. (b) Kiyoi, T.; Seko, N.; Yoshino, K.; Ito, Y. J. Org. Chem. 1993, 58, 5118-5120.
13. (c) Pri-Bar, I.; Schwartz, J. Chem. Commun. 1997, 347-348.
14. Bulka, E.; Ahlers, K. D.; Tucek, E. Chem. Ber. 1967, 100, 1367-1372.
15. Selenolates and selenols are readily oxidized with molecular oxygen to afford the corresponding diselenides: (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697-2699.
16. (b) Sharpless, K. B., Young, M. W. J. Org. Chem. 1975, 40, 947-949. Although the detailed mechanism is not clear, molecular oxygen may act as a four-electron oxidizing agent in the present reaction to give water as the final product.