A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2669-2672

  Batey, Robert A ^a   Yoshina Ishii, Chiaki ^a   Taylor, Scott D ^a   Santhakumar, V ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DECOMPOSITION; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033515774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00302-0     Document Type: Article

References (15)

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3. For an excellent review of azolides, including the uses of CDI and substituted carbonylimidazolium ions as activated reagents, and the formation of carbamates and thiocarbamates, see: Staab, H. A.; Bauer, H.; Schneider, K. M. Azolides in Organic Synthesis and Biochemistry, Wiley-VCH: Weinheim, 1998.
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8. Guibé-Jampel, E.; Bram, G.; Wakselman, M; Vilkas M. Synthetic Commun., 1973, 3, 111-114.
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10. (a) Guibé-Jampel, E.; Bram, G.; Vilkas M. Bull. Soc. Chim. Fr. 1973, 1021-1027.
11. (b) Saha, A. K.; Schultz, P.; Rapoport, H. J. Am. Chem. Soc. 1989, 111, 4856-4859.
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13. 3) δ 153.53, 148.61, 133.51, 130.99, 129.01, 127.48, 127.30, 126.23, 125.27, 121.19, 118.22, 66.33, 66.21, 44.61, 43.86; HRMS (EI) m/e calcd (M+) 257.1052, found 257.1045.
14. 3) δ 168.33, 138.06, 131.32, 128.55, 125.77, 124.86, 124.83, 44.96, 44.187, 33.52, 26.87, 26.17, 25.63, 23.64; HRMS (EI) m/e calcd (M+) 275.1344, found 275.1335.
15. 3) δ 155.56, 143.33, 137.79, 128.55, 125.60, 125.43, 119.29, 62.43, 37.43, 25.50, 17.84; HRMS (EI) m/e calcd (M+) 219.1259, found 219.1251.